“Do I Have to Move to Find a Decent Woman to Date?”

I’m a lonely single father of a 13-year-old son. I’m twice divorced, but it’s been six years since the last split, and I’ve really used that time to figure myself out and I have adjusted my expectations accordingly. I’d love to date again as I miss the company of an engaging, charming companion, but my age seems to be a problem – I’m 53, and I live in a very traditional part of the country. The women my age here are all grandmothers – they are a HARD 50+ (as in their lives have obviously been difficult, and it shows), and I’m just not attracted to them. They aren’t particularly attracted to me either – they’ve raised their kids and are not down with someone who has to put his child first. The single women with kids my son’s age are all in their mid-to-late 30s and want nothing at all to do with a guy my age.

Short of moving, what’s a guy to do? Add in that I’m retired due to a disability (even though I am quite stable financially!), and I’m like dating poison! There HAS to be a cute, attractive, single parent who’d enjoy spending her rare free moments with a nice guy who speaks in full sentences, has all of his own hair and teeth (both well cared-for), and doesn’t have a hygiene problem. But where is she and how do I find her? Dating apps were a bust – I think the women on those apps are looking for a very specific type of guy physically, and it’s apparently not me. (I am always honest 100% about my age, appearance, and disability – I use a cane to get around.)

There used to be meetings for single parents, but I think the Internet has made those a thing of the past. Add in that I’m not at all religious, so church/temple is out. Short of seeing a good looking woman on the street and running her over with my car, I don’t know how to get a girl interested in me! Advice appreciated, thanks so much! — 6’2″, eyes of blue, boo hoo hoo

So, you’re twice divorced, on disability/unemployed, a single dad with a teenage son to care for, opposed to dating apps, in your mid-50s (but don’t want to date a woman your age because, ew, old), and you refer to women you find attractive as “girls.” And you want to know what you can do, short of moving, to find someone you might connect with? I’d say it’s time to adjust your attitude. It’s wonderful that you’ve spent the last six years figuring yourself out and adjusting your expectations, but it sounds like your expectations need to be adjusted further.

If you aren’t attracting women (women, not girls) fifteen to twenty years younger than you, maybe it’s time to start accepting that the women your age who have had hard lives and look it are actually your match, and, as much as it may take effort on your part to see and appreciate the attractive qualities they possess, it may take some effort on their part to totally appreciate the attractive qualities you possess.

I hear a lot of excuses from you: Women your age won’t like you because you have a son at home who is your top priority, women on dating sites are looking for a physical type and you aren’t it (because, apparently, all women are looking for the same exact physical type), there aren’t meetings for single people anymore because of the internet, and you can’t join a church or temple because you aren’t religious. It sounds to me like you’re afraid to actually explore potential options because you aren’t willing to settle for anything other than exactly what you’re looking for and you have a feeling that what you’re looking for is out of your league and you don’t want to face rejection. And, yet, you have no trouble rejecting even the idea of a woman who doesn’t look at least fifteen years younger than you and isn’t pretty enough.

What about a so-so looking 49-year-old who is kind and compassionate and understanding of your single-dad lifestyle and your disability? Is she an automatic “no” simply because she’s not super good-looking? Even though you said that what you miss about dating is sharing the company of someone who is engaging and charming? A 49-year-old woman — a grandmother even — who’s had a hard life and isn’t winning beauty contests can still be engaging and charming. And she might be a wonderful match for you — someone who will make you laugh and feel loved and appreciated, but you’d rather miss out on that and be lonely because you’re holding out for someone young and beautiful.

Revamp your online dating profile so that it highlights your best features and not the ones you think might be turning off potential dates. Rather than be “100% honest” about “your age, appearance and disability,” leave some stuff up to mystery until the first date. You don’t have to be 100% upfront about everything before you meet. (I’m not suggesting you lie, but I am suggesting you withhold some of the more surface things about you — like that you’re 53 and unemployed and walk with a cane — until someone has a chance to get to know a little about who you actually are). And I’m suggesting that you give others a chance to show you who they actually are — what’s in their hearts and what makes them tick — before dismissing them for superficial reasons.

Can’t find a single parent group to join (because the internet ruined them- ha)? Then create one! And, get this — you can use the internet to publicize it. Start a Facebook group in your area for single parents, share a post on Craigslist about it, reach out to area newsletters and online groups who can publish a little blurb about it. Pick a place and a time to have a first meet-up and see who shows up. You can do all that and even Google “single parent groups” in your town to make sure you haven’t missed one that already exists! Spread the word through your son’s school and through friends and acquaintances. And while you’re at it — let people know you’re open to being set up.

Finally, you don’t have to be religious to join a church. Have you heard of Unitarian Universalism? It’s a “liberal religion characterized by a ‘free and responsible search for truth and meaning.'” People in this group “are unified by their shared search for spiritual growth. As such, UU congregations include many agnostics, theists, and atheists among their membership.” If you identify with being liberal, agnostic, a theist, or an atheist, and the pursuit of spiritual growth and search for meaning appeals to you, you may enjoy gathering regularly with like-minded people who might also be open to the possibility of a romantic connection. You can use the internet to find a UU church near you.

Is the internet bad sometimes? Sure. Has it had some negative effects on society and exposed some ugliness that used to be better covered? Absolutely! Any recent thread on Twitter – sorry, X – can illustrate that. But that doesn’t mean it’s been all bad, or that we can’t use the internet for positive gains. (You wrote to an internet advice columnist, after all, so you must believe on some level there is some good to be found online.) I would suggest cultivating and extending a positive attitude not just to the internet, but to dating and socializing in general. There is goodness and positivity to be found, both online and off (and the internet can simply be a tool to connect you to the good offline). But sometimes you have to look a little further than a pretty profile picture to find it.


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If you have a relationship/dating question I can help answer, you can send me your letters at wendy@dearwendy.com.


  1. Ele4phant says:

    Sorry very little sympathy.

    So you are deserving of someone you find hot and therefore reject out of hand women who don’t meet that standard, but it’s a great injustice that the potential partners you want are rejecting you for not meeting their standards? Come one man, do you not see the hypocrisy there?

    I’m sorry, a man in his fifties who has a young son and who is disabled is not attractive to a lot of people; just like a fifty year old grandmother who has had a tough life isn’t going to be considered the hottest woman on the block.

    That’s not to say you need to settle, like Wendy said you probably can find a woman who shares your values your sense of humor your interests yadda yadda yadda. But maybe you’re going to have to give up on dating a hot thirty year old, okay?

    1. ele4phant says:

      Sorry to post again but these lines just really got under my skin:

      There HAS to be a cute, attractive, single parent who’d enjoy spending her rare free moments with a nice guy who speaks in full sentences, has all of his own hair and teeth (both well cared-for), and doesn’t have a hygiene problem.

      So you think because you meet the bare minimum here of having decent hygiene and are of normal intelligence, you deserve a cute attractive women? That’s all you think you need to bring to the table here?

      I’m sorry, but you sir sound like YOU are a hard 50.

      1. RedRoverRedRover says:

        Exactly! And do you know what the single women that he’s interested in are thinking? “There HAS to be a cute, attractive, single parent who’d enjoy spending his rare free moments with a cute, attractive single parent around the same age.”

        Like, seriously. You have to look in your league. The women you want are looking in THEIR league, or maybe above it. You sound like you’re what, maybe a 5 or 6 out of 10? Maybe lower? So if you’re looking for 8’s or even 7’s, it’s not going to happen. Why would a 7 want to date you when they could date a 7?

      2. I know, this all sounds like “I’m so frustrated that all these women are just as superficial as I am!”

      3. I think he’s in his pre-disability age, when being 6’2″, employed with a decent job, and in possession of all his hair and teeth likely were sufficient selling points in his neighborhood. He hasn’t internalized yet that he is now 53 and the world sees him differently than it did when he met his second wife. Then again, two divorces and nonreligious will disqualify him in much of this nation.

        He reminds me of Robert, who offered so little, yet demanded so much.

        Most schools, especially at the middle-school level of a 13-year old have parent organizations: PTA, band parents, booster club, whatever.

        Look to hobby clubs in your area: garden and book clubs both have a large fraction of women.

        Adjust your attitude, as well as your profile, and try on-line again.

  2. dinoceros says:

    You’re framing the issue in two distinct ways. On one hand, you’re saying that women are looking for someone younger, more attractive or whatever than you, so no one wants you. But you’re also saying that you can’t find anyone who is attractive enough for you. It sounds like you’re guilty of the exact thing that you’re upset that the other women are doing.

    I think one thing people forget is that the purpose of online dating is not to deposit a perfect option at your doorstep. The purpose is to increase the number of people you meet so as to make it more probable you’ll meet someone you like. It’s not going to increase the proportion of attractive (or smart or whatever a person is looking for) people from normal life. It’s like shopping in a thrift store. You can find something awesome, but you have to actually search. So, either commit to improving your profile and truly giving women a chance who you might not think are your type (who knows? You might find someone in the same boat as you) or just wait for someone to show up on your door (which is not likely).

  3. Juliecatharine says:

    “Short of seeing a good looking woman on the street and running her over with my car, I don’t know how to get a girl interested in me”…this line turned me off so much. LW I’m sure you were joking but no, just no. Nobody is entitled to find a mate, we’re blessed to find people to share our lives with and they can come in all sorts of packages–some are wrapped beautifully others need a closer look. You’re in your early 50s, financially secure, and a dedicated dad-I find it hard to believe that there aren’t any women in your area who would be interested in seeing what else you have to offer. Don’t start a single parenting group strictly to get a date though-that’s kinda creepy. If you don’t have to work that’s a great opportunity to volunteer. Pick a group that supports a cause you feel strongly about and that is active in your community and get involved. I work part time in animal rescue and there are a lot of people your age who volunteer who are maybe on the very shy end of the social spectrum but who are truly wonderful. Approach women as people first and you never know what could come of it.

  4. LW, I think you should not give up so quickly on everything. You say online dating was a bust. Well, people leave and join every day. You are so quick to categorize things. Women my age or women with sons the same age. You are painting with a broad brush because you are discouraged.
    Here are things your should try. Join clubs or do things that interest you. We live in a world that has something for everyone. Maybe you can’t join active pursuits but what about book clubs, board game leagues, writers workshops, an art class, ect. There are communities out there. Fantasy football leagues. whatever. Once you start expanding your social circle, you can meet people organically who are either dating potential or believe there is someone that might be good for you. Your son is getting older and you will have more and more free time. Start to fill it with your life and new options will open up for you. You will have more positive things to say about yourself and more to offer.

    1. Honestly, why not join the PTA of your son’s school? Just get involved and see what happens. There could be tons of moms that you befriend and they can see about setting you up.

      1. Juliecatharine says:

        PTA involvement is a great idea.

      2. GREAT idea!!! I think getting involved with other activities at the school can def open up some new opportunities. Supervising an after school club, chaperoning an event like a field trip or dance, etc….I know LW says he walks with a cane but still worth putting the idea out there.

      3. Do all places have a PTA? There wasn’t one for my school district. It’s just not something rural schools cared about.

      4. Actually, I don’t know. I was in a bunch of schools growing up and there was always something like that but I always lived in the suburbs. How did your school get parent volunteers for trips and dances?

  5. Sorry guy – it seems like your focus is strictly on the outside.

    You want cute AND attractive…but the best you can say about your own appearance is you have your own teeth and hair? Dude. Shift your focus. Focus on finding calibre people. Join a book club at the library/start a book club at the library. I’m sure your area has meet-ups too – join some that seem to have the appropriate demographics….as in your age – 5 years either way. There is no way every 50 year woman has had a hard life that shows on her face… Anymore than your life shows on yours. What does that even mean? Meth use? I mean draw the line at meth use, by all means. But, just y’know, aging? Um. sign on to aging. Aging is okay. We are all doing it.
    What about Our time? Isn’t that the dating site for people your age? And people wanting to date people your age? Dating is about what you bring to the table and finding your equal. Some people bring beauty. Some bring money. Some bring charm. Some bring humour. Be honest about what you bring and how much cache that garners you. Your own teeth and hair isn’t going to land you a beauty. Might land you a woman with her own teeth and hair too, though. Maybe with a nice smile and a willingness to accommodate your disability and time you have to spend with your young son.

    1. “You want cute AND attractive…but the best you can say about your own appearance is you have your own teeth and hair?” –> Haha, exactly!!

  6. Avatar photo Moneypenny says:

    This dude sounds kind of condescending to me. Women his age aren’t up to his *standards*? From how he’s describing it, it makes me think that he lives in a town where all of the women lose their teeth after age 50 or something. Lower your standards. Date outside your type. You might be surprised what you find.
    Also, meetups, PTA, volunteering.

  7. Ok I think everyone is being a little hard on this guy. I didn’t take his comments on women his age that bad because I got the idea perhaps he moved to a small town “traditional” where people CAN lead harder lives, and the extracurricular activities are limited. I’m from a small town and the difference in education and appearance is noticeable between those that have lived there their whole lives and those that haven’t. if this guy is living in a more secluded part of the country, then he’s going to need the Internet even more to find someone.

    1. ele4phant says:

      Eh, but the thing is it sounds like he has lived a hard life too. There’s no indication that he’s NOT from where he currently lives, and even if he is he’s not above his peers, you know? He’s got a lot of qualifiers that would make people find him less than a desirable person, just like his female peers. And yet, he wants someone he finds attractive with little regard to the fact that who he finds most desirable may not desire him.

      And I’d be more understanding if he had said something more along the lines of “The women who are may age are at a different stage of their lives and aren’t interested in dating me; whereas the women who ARE in the same stage of life as me aren’t willing to considering dating an older guy.”

      But he lead with looks (these women are a HARD 50). And furthermore, he seems to feel entitled to his ideal partner (cute attractive women) because he meets the bare minimum (good hygiene, has teeth and hair, reasonably intelligent).

      It’s all about what he wants, little about what he brings to the table.

      1. Avatar photo Dear Wendy says:


    2. dinoceros says:

      I mean, yeah, but it’s where he lives and judging everyone (while also complaining that they are judging him) is not going to help him. He seems to be fine with younger women in that area, but his concern is that women his age look older than what he’d want. If he’s from a more cosmopolitan area, then maybe he’s used to women spending more money on their appearance to look younger, sure. But this is where he lives now, and if he wants people to give him a chance despite his age, then he needs to do the same.

      1. ele4phant says:

        True, assuming the younger women and older women in his area are all generally from the same background, his only objection to the older women is how they look, not their interests, personalities, or educational attainment.

        And on some level, I get it. We all want to be with people we find attractive, but we also have to be realistic about who *we* attract. It’s kind of rich for him to want young women to look past his physical short-comings while not extending the same courtesy to women his own age.

  8. I’m in my mid-30’s and I tend to usually be attracted to older men, however I can tell by the way that you write about women and what you are looking for in women, that I would have absolutely no interest in you. It wouldn’t have anything to do with the fact that you are disabled physically, it would be 100% your emotional disability. If a woman my age were interested in dating a man your age it’s because we want a mature, quality man with a strong character who can be a good companion (which can sometimes be difficult to find in men in their 30’s). However, you are eliminating yourself from that group because you apparently, based on your superficial priorities, are just looking for arm candy instead of a companion with a deep connection….. THAT is what makes you unattractive to women my age.

  9. Another Jen says:

    Wow. A lot of the things you said are really mean and judgmental. Coming up through a hard life is nothing to scoff at…challenging experiences may yield strong, passionate, interesting people. A woman had children young, worked hard, and has grandchildren in her life might be a lot of fun.

    Imagine if someone was as dismissive about your life history as you are about “hard 50” women. After all, there are people who might make unkind assumptions about not having a job, being twice-divorced, etc.

    Maybe the answer is to try to meet people you can have a good time with…not just look for cute girls willing to date an older man. You might be surprised how attractive a great smile, good stories, and a life experience that’s different from yours can be.


    You also seem like one of those guys who

  10. ugh…..you have the most yuckiest personality LW….it comes across so clear in your letter…..if you are wondering why you are single, start with that……also no one is attracted to a condescending and shallow person (you only seem interested in a persons appearance or at least that is how it comes across)…..god help any woman who gives you the time of day….blech!

  11. Put quite simply: you’re aiming out of your league.

  12. Sue Jones says:

    Actually I do have some sympathy for the LW. I am 55 and live in a part of the country where women have children later because they are finishing their education and who eat well and exercise so in general 50 here looks younger and fitter than 50 elsewhere. So maybe you do have to move… But that aside, try meet ups and clubs and other interest groups to find like minded friends. I also have a 13 year old and I am finding that they get a little more independent so there is time to do that stuff. That just makes you a more interesting person period. And interesting people are more attractive.

  13. Much love to Wendy for suggesting UU! I identify as an atheist and, sometimes, I go to the local UU church just to discuss spiritualism and life and all that jazz, and it’s super nice. The people there are very, very welcoming and sweet and come from all sorts of walks of life – highly recommended if that’s your feeling.

  14. Baccalieu says:

    It seems to me that the people who are bashing this guy are overlooking the fact that you can’t really control who you are attracted to. I have some sympathy for this guy and I at least want to give him credit for being honest even if it does expose him to everyone’s disgust. I am also not very much in the looks department and I have not been in many (or any) good relationships because I have trouble finding someone that I want to be with who wants to be with me. It’s all very well to talk about how we should look to the person’s inner beauty and not mind about their looks (and with respect to my friends I really don’t care what they look like) but in practice, for a romantic partner, I and, I think, most people want someone who they are physically attracted to. Believe me, I get the hypocrisy, but understanding that it is hypocritical does not mean that you can simply change who you find attractive. I’d like to ask people who say just date people who, like you, aren’t attractive, how do you do that? Can any of you tell me that you managed to do it? (“I used to date hot guys who were jerks, but one day I decided to give a plain but very nice guy a chance and now I’m completely in love with him and I think he’s a total stud.” or the reverse “I used to ask out hot girls who weren’t really interested in me but I decided to start asking out girls I didn’t find attractive and I found my wife and now I think she’s the sexiest woman alive.” Does this happen? And, if so, how?) Once again, I’m making a post that is going to come across as trolling, but it isn’t. I am genuinely asking because I have been struggling with this my whole life. Ugly people, like myself and the LW, have been brought up in this culture to find the same things attractive that everyone else does. How do we change that? The people who are saying to this guy, “You are being a pig and you should stop looking for someone you find attractive and date someone at your own level of attractiveness” are not really being that enlightened. Aren’t they really saying, “You ugly people should just go away and breed amongst yourselves and leave us beautiful people alone.”

    1. ele4phant says:

      a) It’s a relatively common phenomena for people to find their partner more attractive once they get to know them. Turn someone you initially find physically repulsive into a total stud after getting to know them? Maybe not. But certainly plenty of people have found their attraction went from “Hmm, okay” to “Wow, that person is amazing” after they got to know them better. See – me and my husband. He’s objectively pretty cute, but not my type and I didn’t notice him for months. It was once we started talking that things really took off.

      and b) it’s fine to recognize you are attracted primarily (only?) to people who do not reciporicate, but the answer is then you just don’t date. If you’re so self-aware that you know there’s possibly no way you could possibly give someone who is arguably as attractive you a chance, then you need to be self-aware you won’t get to date anyone. No one is entitled to the partner of their dreams. If your dream partner isn’t realistic for you, that means you accept you don’t get a partner; it does not mean someone else has to settle for you.

      And finally, I don’t think this relates to the letter writer, but I want to address this:

      Aren’t they really saying, “You ugly people should just go away and breed amongst yourselves and leave us beautiful people alone.”

      I would say that people should not pursue, harass, or feel entitled to the attentions of people who are not attracted back. It does not sound at all like this letter writer is harassing anyone, but on a basic level, yes, leave people alone if they do not reciprocate your interest. That’s pretty basic.

      1. Baccalieu says:

        I really want to reply to your last point. I never in way suggested that I thought it was okay to harass someone. That is not what I was saying and I think you are twisting my words. Maybe that’s payback for my putting a spin on the things that the others were saying, but it seemed to me that everyone was entirely too comfortable with pointing out to this guy that he was no physical prize himself (for example, everyone seems to accept as a given that his disability makes him less attractive as a dating partner) while telling him that he really needs to open his mind to people’s inner beauty. My point was the implication of these statements was “you uglies should stick with your own kind.” You are welcome to disagree, but do you really have to accuse me championing harassment?

      2. ele4phant says:

        What are you saying though?

        I’m saying this guy needs to look beyond the physical and see if he can’t form connections beyond what he initially thinks he is capable of.

        Try it, it works all the time. People meet, don’t initially feel a huge spark because they may not feel an attraction right off the bat but they discover over getting to know the person better. Like I said it’s COMMON. You do have to try, and yeah, maybe go out on a date with someone who isn’t immediately your cup of tea. This guy sounds like he can’t get past the physical, so yeah, I’m going to chastisize him, or anyone, who just starts with “Oh whoa is me, all the people I find attractive don’t find me attractive! What to do?”.

        What you do is push yourself to know people a little better. You might surprise yourself.

        And also, physical attraction, while important, is fleeting. Even if you do manage to land the hottest girl you could imagine, we all like the shiny new thing and attraction fades. Plus, we all just…age and look less attractive over time. If you are incapable of pushing yourself to look for qualities beyond looks, you will fail to maintain relationships.

        Are you truly telling me it is impossible for you to even entertain the idea of forming a connection with someone who doesn’t immediately make your heart race? If so, I would say you have a very narrow view of what relationships and attraction (full attraction that pertains to every aspect of your partner) are about.

      3. Baccalieu says:

        No, I’m not saying I can’t entertain the possibility of a connection with someone that doesn’t make my heart race, in fact, that is what I have been trying to do for the past twenty years or so, but if you are not much in the looks department you are not going to get that many opportunities to develop a connection because people won’t say yes to you. And also it’s one thing to ask out someone you think is “um, okay” and hope that they grow on you and another to ask out someone you think is ugly. You rather undermined your own argument when you said your husband, even though you weren’t attracted to him was “objectively cute”. People like me (and, I suspect, the LW) are not objectively cute. In fact, we are objectively “not cute” yet we are socialized (or genetically programmed) to find the same things attractive that everyone else does. And, funnily enough, I do want to find a partner that I am attracted to. You may say but that’s just the way it is and I have to live with it, but it still really sucks. And THAT is my point.
        Also (and this may sound like more “Woe is me.” handwringing) I think this is harder for guys because (for the most part) we are the ones that do the asking. For a woman to stretch herself the way you suggest, all she has to do is accept some invitations she would normally turn down. But it takes a lot of nerve to ask someone out and risk rejection. (Try being a guy doing online dating and spend a weekend evening crafting a nice personalized message to twenty different woman whose profiles you like and getting 17 no replies, one polite no, one not-so-polite no and one positive reply that after a few exchanges peters out or (very occasionally) results in a meeting for coffee at the end of which she says she’s not really feeling it and leaves with the parting shot, “You’re not really 5-foot-6, are you?” (I really think I am and, if I was going to lie, surely I would say I’m taller than that.) Do that for a few weekends and tell me if your self-esteem isn’t in the toilet.) It is hard to work up that nerve for someone you feel “meh” about. Plus, while this might be getting ahead of myself, when you ask a woman out she will not unreasonably assume that you are attracted to her and if, after a couple of dates, you tell her, “Sorry, I’m just not feeling it” that seems like a fairly shitty thing to do.

      4. ele4phant says:

        Look, I’m sorry I’ve come off harsh.

        And I do want to acknowledge that your (and this guy’s) situation does sound incredibly frustrating and shitty. That does suck, and I should have tried harder to see where you were coming from.

        But I can also hope you can appreciate where a lot of women are coming from here. It also really sucks to have a lifetime of men demanding your attention and demanding you give them a chance, because they find you attractive and deserve a shot because “they’re good guys”. And then dealing with their outrage and injured egos when you reject them. It is infuriating when it’s not exhausting.

        It is hard not to get callous and dismissive, it’s hard not to see the echos of your own personal experiences when you read a post like this one.

        So I hope you can appreciate the lived experience lots of us have had here, and how that’s informing how we’re reacting. How just a whiff of a guy complaining he can’t get the pretty girls he wants sets us off.

      5. RedRoverRedRover says:

        Also, to add to what ele4phant said….

        “all she has to do is accept some invitations she would normally turn down”
        just shows how completely unaware you are of what unattractive women are going through. Unattractive women have NO invitations. They sit there, night after night, with nothing. And if you think it’s hard for you to send out requests to women, just think how much harder it is for an unattractive woman to do it. It’s not as socially acceptable in the first place, and in the second place she’s dealing with, sorry to say, guys like you who aren’t even going to consider her. At least women DO more often take a chance on a guy who they don’t think is attractive. And guys can increase their attractiveness by things like being funny, being musically talented, etc, whereas ugly women typically cannot.

        I know you have it hard, and that sucks, but please stop talking about how much harder it is for you than it is for ugly women. I don’t know why you see a point in even bringing it up, since whether it’s true or not it doesn’t change your situation in the slightest.

      6. also, even as a pretty woman, you’re constantly reminded that your age diminishes your attractiveness in the eyes of many men.

      7. RedRoverRedRover says:

        True. Our “value” is fleeting, whereas men’s can actually increase if they make decent money.

    2. I totally get where you’re coming from, but I don’t really think other people are saying to date someone you find ugly. But sometimes, attraction does grow once you get to know someone! My first love, someone I loved with all my heart, I actually said out loud to my friend the night I met him “That dude’s pretty ugly.” But then we spent some time alone together outside the party talking, and he made me laugh and he seemed so nice. And as we got to know each other over time, I couldn’t remember why I had ever thought he wasn’t attractive! Years later, we’ve long since broken up and he’s married with his own family now, but when I see him pop up on Facebook from time to time, I still think he’s a very handsome dude.

      Similar story, I went on a date with a guy last year and on our first date I thought, wow he looks like such a nerd. By the end of 3 days, I thought he was so incredibly cute and couldn’t remember what I thought was nerdy about him.

      So yes, it’s quite possible to become more attracted to someone over time as you get to know them. Does that mean you’ll become attracted to anybody and everybody you think is butt ugly? No, probably not. But if there’s someone you think is so/so, you might surprise yourself how much better they look after a radiant personality has the chance to shine through.

      That’s definitely harder to do online because you’re just looking at a photo and basically judging the book by the cover. So I get the frustration :-/

    3. RedRoverRedRover says:

      Well, tons of ugly people are married, so there’s that. And I’m sure the majority of them find their spouse attractive. Clearly it’s possible.

      How do you do it? The same way women are constantly told to do it – give people a chance. And I do mean constantly. In fact that’s exactly what LW is doing – he’s whining because women aren’t doing what they’re “supposed” to do and give a nice guy a chance. Well he (and you) need to do exactly that. The best way to do it is to meet women in a non-romantic setting and make acquaintances and friends. This is how I met the majority of my boyfriends, and while I wouldn’t say there were any that I thought were downright ugly, there were definitely ones that I didn’t find attractive until I got to know them.

      As for being hard on this guy, if you knew how often women heard this kind of stuff you might understand why many of us have little patience with it. If you think being an ugly guy is hard, just try being an ugly woman. That’s the bottom of the dating barrel, right there.

    4. Avatar photo Skyblossom says:

      Part of the problem that no one has mentioned was that he has a son who is thirteen and the women his age have kids that are grown and don’t want to get involved with a man with a teenager. They are in a different phase of life. They’ve been there and done the teenage kid thing and they aren’t interested in doing it again. Teens are probably the worst at accepting a parent’s new relationship.

      He doesn’t find the women attractive and they don’t find him attractive. He’s been honest that it goes both ways. I don’t think he is picking on women. He’s being honest. Even if he goes out with an unattractive woman who also finds him unattractive, how will he make them want to be with a guy who has a teenage son?

      I know women who are my age, early fifties, who tell people that if anything happens to their husband they don’t want another man. They don’t want someone who they will need to take care of. They certainly don’t want someone who is already physically handicapped because that seems like to much work and care taking. Men’s health often declines sooner than women’s health and women are looking at the men needing their hip replacements and their knee replacements and their enlarged prostates and their impotence and thinking why bother with all of that when I already have a family. Many women would rather focus on their kids and grandkids. They don’t want to end up with a guy just to find themselves his maid and caretaker. Women are wary of that.

      1. Avatar photo Skyblossom says:

        LW The other thing to keep in mind is that if you’ve been living in this community people know about your divorces and why they happened. If you cheated on one or both ex-wives the women will know it. If you were addicted to porn they will know it. If you had a temper they will know it. If you spent your money on yourself and left the wife to support the household they will know it. If you were lazy and did nothing to help around the house they will know it. You may have figured yourself out but the women where you live will know the full you including any ugly character flaws that you may have or had. I also think women my age are wary of men who’ve been divorce twice. It shows they aren’t good at relationships and who wants to get involved with that. Women are wary of becoming the third ex wife.

        My uncle got married for the first and only time when he was 52. He met his wife, who was a widow, at the local community baseball games where they both went to watch the kids play. They ended up sitting in the stands near enough to each other to talk and then started sitting together to talk. You are most apt to find someone by being social. Go to places where there are people and talk with those around you. Be an overall nice person. If you have an overall bad reputation as a spouse you will have to prove that you have changed by being a great all around person day in and day out. Be thoughtful and kind to everyone. Be warm and friendly to everyone. Be courteous to everyone.

      2. Avatar photo Skyblossom says:

        One more thing LW. I work with women whose husbands are already retired. Some of those women go home to a clean house and a home cooked meal. Some go home to do that for their husband who has been home all day. The ones who work all day and then go home to cook resent it a great deal. They don’t talk about their husbands in the same happy way that the women whose husbands cook and clean and shop do. It is eye opening to see the imbalance and expectations in some of these marriages. I don’t know anyone who wants to get into a relationship like that. Women your age are going to be working. They have no desire to come home to a guy who is waiting for them to cook dinner and then he’ll watch tv while she does the dishes and some laundry. If you want to make yourself more attractive to women you need to specify that although you don’t go to work because of your disability you’ll be happy to cook and clean. I can’t emphasize enough how wary women of my age are of ending up in a situation like this. They want to know that if they are working you will contribute in an equal manner by cooking, cleaning, doing laundry and shopping.

    5. I haven’t read all the responses to your statement, but I wanted to say… I think it’s kind of bullshit.

      Take me for instance. The person who I’m utterly and totally in love with and who I’ll spend a lifetime with isn’t conventionally attractive. He has a skin problem and a lot of cysts. The first time I met him, I thought it was kind of gross. And then I got to know him. You know what? He’s incredibly kind and witty and smart. And now I find him completely attractive and there is chemistry.

      I once called off an engagement to a perfectly kind, smart and attractive fellow, but there was no chemistry.

      So, this kind of thinking doesn’t wash with me.

  15. Anecdata, but: I have decreased lung capacity (50% of normal). I had a guy last year tell me he didn’t want to date me because he wanted someone who could keep up with him on hikes (and we had just gotten back from a hike).

    Yes, it’s a hugely dick thing to say but do you know what it told me? I’m better off without him.

    I’m going to agree with what others have said here and I think the answer is to get out and find friends and see what might develop from there. Online dating can be very superficial and it’s obvious that’s the case here, too. Personally, I’ve had two instances so far where I’ve met a guy and initially was not attracted to him at all but after spending lots of time with him, I developed really strong feelings because he was witty/hilarious/charming/we got to be really good friends, had similar interests, and clicked. It surprised me both times but it really happened! Neither of these guys were my physical “type” at all and I would have “swiped left” on both of them on a dating site, no question. After getting to know them, though, they both became two of my closest friends and we had mutual feelings for each other both times.

    Also: why does the woman you’re looking for have to be a single mom? That really stood out to me. I had a single dad reject me once because I DON’T have kids. I mean, what’s up with that?

    1. RedRoverRedRover says:

      I once had a guy unloose a spiel on me about women rejecting him because he had kids and I should give him a chance. Like, first, why would you want to date someone who doesn’t want to date a guy with kids, and second, why would you getting mad at me make me want to date you?

      Anyway, maybe this guy’s experienced that and only wants women who he knows are cool with having kids

  16. Baccalieu says:

    Sorry, for having to put up with my venting. I’m the same age as the LW (almost) and his story and the responses hit a nerve. Red Rover, I never meant to suggest that it was only unattractive guys who have it hard. I agree with you that in many ways (maybe in all ways) women who are not conventionally attractive have it worse. I am aware that there are people who are much worse off than me and I try to focus on that.
    Ele4phant, I can certainly understand (at least intellectually) that it is tremendously irritating (and often more than irritating) to continuously fend off unwanted advances and to deal with the hurt feelings that arise when you turn down someone, which you have a perfect right to do. I am sure that if I were magically transformed into an attractive woman I would be just as upset about unwanted advances as everyone else, but from where I sit it is very hard not to think that it would be nice to have the problem of being pursued too much at least for a little while. (“Damn it! All these women just keep coming on to me and they won’t stop even when I turn them down. It’s like they feel entitled to have sex with me.” – I am being facetious, of course – I know it is a serious problem).
    It is nice to hear from those of you have stories of growing attracted to someone you did not find attractive at first. (and, Red Rover, it’s true that lots of ugly people are married.) It is helpful to hear that. I just have to figure out a way to get into that situation for me. And I do get that it is pointless for me to just keep shouting about a problem that is basically insoluble, and I will (and I think I do) try not to overdo it. But, Red Rover, I hope you don’t mean it when you ask me not to talk about it at all. I see Dear Wendy as a place where you can talk about your problems and maybe get some support or occasionally even some advice that is actually helpful and I hope that’s true.

    1. ele4phant says:

      I appreciate your reply.

      As a gentle reminder, I would say constantly fending off unwanted attention is generally more than tremendously irritating. I can understand when you have a lack of attention, it might almost seem like a nice problem to have, but it’s not. Not at all.

      Women’s physical safety is often threatened. And even though most guys would never ever ever think to harm a women for rejecting them, as a woman you can never predict which is the guy that’s going to off on you and which is the guy that will gracefully accept your rejection. So each and every time you find yourself in one of these situations, there’s fear. Fear that this is going to be the guy that won’t leave you alone, that stalks you, that screams at you, or god forbid, actually gets physical with you.

      You never know what you’re going to get. And getting put in this situation over and over again is more than irritating.

      1. I don’t know. I’m pretty sure I’ve gotten as much attention as the next woman, and my friends lament that I’m the one that always gets hit on when we’re out somewhere – but I’ve never really gotten the whole complaining about it being so annoying thing. Maybe that’s how others feel, but to me that always felt a bit like bragging. And I’ve never felt my physical safety threatened when getting messaged online or when a guy nicely walks up to me to talk (especially when I have other people around). Yes, every so often a guy is a complete dick, or tries to follow you, or whatever – that’s absolutely not okay. But when a guy tries to nicely and politely talk to you, I don’t think they should be made to feel like there’s anything wrong with that. In my opinion women’s rejections are oftentimes way too harsh (again, just in my experience, I’ve often seen that and figured the woman was just trying to show off to her friends by acting sooo uninterested that she can’t even be nice about it).

      2. Anyway I guess my point is that for me, I tend to find it flattering rather than “tremendously irritating,” as long as the guy is not a dick!

      3. ele4phant says:

        To each their own. I hate it, and now that I’m in my thirties I’m sick of this shit already.

        And the vast majority of the time, guys have been respectful. But after a few incidents of getting screamed at, or harassed, or just not taking a damn hint, that’s enough to put me on edge on each and every time I get approached.

        A not small part of me can’t wait to be “too old” (or maybe even a hard 50!) and be left alone already.

      4. ele4phant says:

        And I will say, I’m probably pretty bitchy when I turn guys down now.

        So sorry to the well-intended and genuinely nice guys, I guess, but I’m definitely not harsh to show off to my friends (I usually am harshest when I get approached when I’m by myself – that’s when the fight or flight really kicks in I guess).

        But, at this time in my life I’m just over it, and I’m not going to be nice about it anymore.

      5. RedRoverRedRover says:

        I would imagine it’s highly dependent on early experiences. The first two times I can remember being complimented were both by very creepy older guys and I was way too young (like 13-14 to their mid-30s or 40s). It was very scary and I didn’t know what to do. And I was never even touched or anything like a lot of young girls are, but it definitely made me anxious right from the beginning about men approaching me.

        Count yourself lucky that you’ve always felt safe enough that your automatic response is not fear. Not all of us have.

      6. I’m sorry that happened to you. And I’m not trying to discredit what you’re saying – we all carry around things that have happened to us differently. But your assumption that my attitude is because I’ve “always felt safe enough” is completely off-base – I’ve faced numerous creepy instances and have been assaulted. But I guess I’m lucky in that each time a guy talks to me it isn’t triggering for me, and I’m still able to see each person as an individual human.

      7. RedRoverRedRover says:

        I see them as individual humans, but I can’t help it if I’m on guard. And it’s happened often enough since those first instances to keep me on guard.

      8. I’m actually completely stand offish to anyone who approaches me, whether they’re attractive or not. And whether I’m alone or not. I’m uncomfortable with extra attention. I’ve 100% shut down conventionally attractive men who have approached me. It’s not that I’m trying to be mean or rude. It’s a comfort level thing.

      9. ele4phant says:

        I can appreciate that we are all different people and we react to the same situations differently.

        I completely accept that your responses to men that approach you are completely authentic, despite the fact that we’ve had very similar life experiences and I personally react an entirely different way than you.

        By the same token, you kind of did the same thing RedRover did to you. You look at women reacting negatively to unwanted attention, and interpret it as bragging, or that we are reacting too harshly to attention we don’t want.

        It’s not bragging, it’s not a show for our friends, it’s just as a genuine a reaction as yours.

        And I kind of feel it’s damaging to put it that out there. I feel like those “nice guys” of the world hear one woman say “Oh, girls who tell you to piss off are really just showing off to their friends, it’s actually flattering to get male attention”, and they feel encouraged to keep up what they’ve been doing.

        We’re not bragging. We don’t like it. It’s fine you find it flattering – I believe you – but please don’t question how I might respond.

      10. RedRoverRedRover says:

        Yes, thank you! This is what I was trying to get at but I didn’t know how to do it.

      11. Was not trying to make it come off like I was questioning YOUR intentions or feelings. I don’t. And I get your stance. That’s why I specifically said that I’m not discrediting RedRover. Sorry if it came off that way. I was just observing that in general I think SOME women feel pressure to reject guys because they think they have to for appearances to others around them. And I was pointing out that I can’t relate to what you guys feel – that doesn’t make either of us wrong.

    2. RedRoverRedRover says:

      I didn’t tell you to stop talking about your problems, I told you to specifically stop saying that you have it harder than ugly women. For two reasons: 1) I doubt very much if it’s true, but more importantly 2) it’s going to feed bitterness. It will make you angry at women, which will make women not want you, which will make you angry at women…. do you see?

      I think you’ve gotten some good advice here, from me and others. I have dated unconventionally attractive guys, and I have been interested in unattractive guys who have blown me off (I’m conventionally attractive). Looks matter, but I don’t think it’s as much as you think, particularly if you’re a guy. Also I’m 5’8″ and have dated 5’6″ guys. And one of my husband’s best friends is like 5’4″, maybe less, and he recently got married to a very pretty tall woman. And, like I said, ugly people get married all the time.

      I don’t want to go all armchair psychologist on you, but you do seem fixated on the idea that you’re ugly. And I’ll tell you this – no one who is beautiful on the inside is ugly on the outside. No one. It shines through. But people have to see the inside, and that’s why they have to get to know you first. It sucks that it’s an extra hurdle that you have to jump that attractive people don’t, but it’s not an insurmountable hurdle. It takes some work but you can get over it.

      And the magic thing that happens is that while you’re letting people get to know you and see the attractiveness in you, the exact same thing will be happening with them. You’ll be getting to know them and see the attractiveness in them. And at that point conventional attractiveness won’t matter anymore, because you’ll each think the other is so wonderful. That’s how it works, even for attractive people. You just have to start getting to know people, and forget about what you look like for a bit.

      1. Baccalieu says:

        I was about to say “Where did I say that ugly men had it worse than ugly women?” But when I looked back at my posts I saw it. I didn’t put it very well but I didn’t mean that ugly men in general have a harder time dating than ugly woman, I meant that it isn’t easy for an ugly man to follow the advice that he should simply go after less conventionally attractive women. But, even there, you are 100% right that it is not just hard, but impossible, when you are waiting to be asked and nobody asks.
        As far as being ugly is concerned, I don’t mean to focus on it too much or exaggerate it (I know that I’m not deformed and I don’t frighten small children) but nevertheless as a prospective mate, physical attractiveness is not my biggest selling point. I do believe that I have many good qualities, but I am not going to get a chance to display them if no one will give me the first date. You are right about the feedback loop where getting rejected makes you depressed and saps your confidence (and, yes, makes you bitter) which makes you still less attractive, but just knowing about it doesn’t enable you to just flick a switch and be positive and confident. That is the difficult part.
        Anyway, I am actually glad that this thread has kept going because I think it is an important topic and I want to learn more about how woman (and men) feel about approaches and initial romantic interactions. On-line dating does have the advantage (I think) of not having to worry about coming off as threatening or bothersome (at least if you can take no for an answer). Also, you know that the women are at least looking for a partner. However, the big disadvantage is that you are judged primarily on your looks, as Ms. Dre says, and therefore it may not be right for me. But I’d like to ask the people who find the personal approaches frightening or harshly turn them down, how would you like to be approached, assuming you were looking for someone (or, Ele4phant, is the answer simply DON’T)?

    3. You asked above for anecdotes, so maybe I can provide you with one. I am a conventionally attractive woman, and my boyfriend is not really that conventionally attractive (he had a lot of trouble finding women to date before meeting me, and faced the same problem you describe, of messaging a bunch of people and getting nothing back). But he’s brilliant and funny and caring – there were a whole host of great qualities that came out pretty fast, and for that reason I was attracted to him right away, and then he just got increasingly more attractive to me.

      I get that it’s hard, and I’m sorry for that. We live in a very superficial society. I think the one piece of advice I can give is that when you’re on a date or talking to a woman, you need to not have the whole “I’m ugly and not good enough” worry hanging over your head, because that will just stop your good qualities from shining through. My impression just from what you wrote here is that you are honest, funny (you made me chuckle with your “it’s like these women feel entitled to have sex with me” line), thoughtful, and bold enough to re-post to bring attention back to the point you were making after getting kind of attacked above. In addition to physically taking care of yourself as best you can (I feel like you can really do a lot with whatever you were naturally given just by taking care of yourself and dressing well), I think the key is to not worry about it and just let your good qualities emanate. It’s hard, but be excited to be talking to someone you’re interested in, and show her you’re really interested in what she’s saying, rather than being preoccupied thinking about how she’ll probably fade out on you. Maybe it will take a little while, but I know there have to be other women out there who would be excited to meet a great guy and not be too caught up in the superficialities.

  17. Addie Pray says:

    I have the solution for ugly men who want to date only beautiful women: become a lawyer. From what I’ve personally seen, it’s 100% effective!

    1. RedRoverRedRover says:

      Yeah, but then you’re a lawyer. I kid, I kid! 😉

      1. Avatar photo Addie Pray says:

        Sadly, the law degree does not work the same for ugly women who want to date only hot men, haha. (More “evidence” to your point that ugly women have it harder; I mean, getting a law degree is not so hard, and it’s 100% effective (for men looking for beautiful women)).

      2. RedRoverRedRover says:


        On another note, I’ve been having horrible sleep issues with my daughter, and I’ve been rereading that book I recommended… it’s fantastic. I misremembered, it’s not actually about how to cry it out. He talks about that, but he also talks about no-cry and some-cry as well. The book is more of a whole overview on the study of infant/toddler/child sleep, and how it all works, and what the effects of bad sleep are, and what a good schedule is and what its effects are, and how to get there. Seriously, fantastic. And the guy who wrote it is a pediatrician and all his theories are based on his own studies and the studies of other doctors who study sleep. Not like some of those others that are just “this worked for me, try it!”. It’s got hard evidence to back it up.

        Healthy Sleep Habits, Happy Child by Dr Marc Weissbluth. You won’t be sorry, really.

  18. LW, why is moving such a last-ditch option? That’s an honest question. Is it that you have family there? Or your soon likes it there and you don’t want to uproot him? Because putting all the other issues aside, maybe moving really would help! If you’re not meeting a group of peers that you really jive with where you are, maybe your people are elsewhere. And I do get it – in a lot of places, people do not take as good of care of themselves, and so by 50 seem a lot older. Why not move somewhere where there is just a bigger dating pool, and where people are living the type of lifestyle you want? That might truly be the best option.

    Unfortunately, and I’m sorry for jumping to conclusions about this, but to be really honest it’s your disability that I find to be the catch. It would be one thing if you were saying that you wanted a similarly-aged woman who could keep up with your active lifestyle or something, and that the 50 year olds you’re meeting are not in good enough shape. But since you walk with a cane, your trouble isn’t finding people to go running with. So that’s what makes me think that the ONLY thing you’re concerned about is looks. And I think the problem for you if you move and finally find your golden field of active, spry 50 years old women, is that they won’t necessarily want to date you if you can’t keep up with them… so maybe we’re back to the whole adjusting expectations thing.

  19. Monkeysmommy says:

    I am mid-thirties, have kids, and am (IMO) reasonably attractive. If I were single, I would not be interested in you as you describe. I would be looking for a man who could get oit and be active with me and my kids. Someone who could keep up with my crazy travel schedule, and understand the demands of school and work. You do not meet any of this criteria. Having your teeth doesn’t mean shit if you cannot chase my 6 year old around the park. I don’t care about the age, it is your whole attitude and outlook. Other women, I’m sorry, girls you are looking for are going to have similar views most likely. Sorry, but YOU sound like a rough 50. For perspective, my father is early 50s; he works full time, travels, and is sure as hell not collecting disability. Get to know the women you are passing up on- maybe they won’t judge YOU as hard.

  20. LW, You are a man who doesn’t see women as human beings. You see them as a fancy household appliance to cook, clean and be a bang maid. You see them as a possession, not living being. Women can sense that about a man and it creeps them out.

  21. I find it difficult to understand people making statements that this or that person is ugly. Attraction is not a “one size fits all”. Yes,there are some typical standards of beauty, i suppose, but even those don’t work for everyone.
    I agree that when you get to know someone and you click and have lots in common,then that person becomes very attractive. Women may tend to use this approach more than men, but it really is a good way to go. Values,common interests and integrity, kindness etc.will outlast looks every time, in the long run.
    Ugly,beautiful, pretty, handsome etc. are concepts that are very subjective and personal. Be open minded,maybe date against “type” and you may have more success.

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