“My New Boyfriend Isn’t Handsome Enough”

New readers, welcome to Dear Wendy, a relationship advice blog. Read some of the most popular Dear Wendy posts here. If you don’t find the info you need in this column, please visit the Dear Wendy archives or the forums (you can even start your own thread), do a search in the search bar, or submit a question for advice at wendy(AT)dearwendy.com.

My boyfriend Mike and I have been dating for around five months. He treats me well and we connect on so many levels, physically and mentally. I’m 44 and I was ready for something serious, so I went online and we’ve been dating ever since. The only thing that bothers me about Mike is that he isn’t as good-looking as my previous boyfriends.

You might say they’re previous for a reason. Well, it’s me that did the dumping because I wanted to be free and enjoy the single life. And I was compatible with some of them. Looking back, I can’t believe I dumped them. I guess a relationship wasn’t so important back then.

Prior to meeting Mike, I had several men interested in me. They were also better looking than he is. But I was unfocused/selfish/immature, and I used to treat handsome guys who were interested in me with contempt. I thought I’d bump into them again like I always would at the local bar. I thought they’d still be single. But these men are now in relationships, so I missed my chance. How naive to think they wouldn’t meet someone else!

Mike is smart, has a good personality, and is very open. He ticks most of the boxes except he’s not handsome enough. He’s not ugly, just average looking. I sound crazy shallow, but I don’t believe I am. I’m just human. I suppose I want people to say “Hey, he’s handsome,” but they may not think that with Mike. He hasn’t met my friends or family as yet. If we continue dating, it will eventually have to happen.

I realize that looks fade and I’ll eventually age and so will my partner, but I thought I’d end up with a better-looking man. Do you think I’m settling? Do you think I can get past this?

FYI, we’ve booked to go on a short holiday together (a week). — A Bigger Catch

Do I think you, a 44-year-old single woman who has admittedly missed her chance at relationships with multiple guys because she was unfocused, selfish, immature, and treated men with contempt, is settling for a man who is smart, has a good personality, and is actually interested in pursuing a relationship with you? Hell, no! I think you’re lucky to have him, from the sounds of it. Honestly, HE might be settling to be with you.

You think 44-year-old single women who are entitled and shallow are in high demand? Because, I assure you, men are not usually clamoring for 44-year-old women who think they’re all that and deserve the most handsome and hottest. At 44, if you want the hottest guy in the room, you better be fucking stunning yourself. Like, movie star good looks. And if you have that, you still need to have the personality to go with it to attract a guy who is also the full package.

I’m not faulting you for not being attracted to someone (if that’s even the case), but I am judging you for prioritizing your friends’ and family’s opinions about the appearance of your boyfriend. I think it says a lot about your character and priorities that you place so much importance on your friends thinking your boyfriend is hot. That’s how teenagers think, not grown-ass women who are serious about wanting a committed relationship.

So… maybe you don’t want a committed relationship? Is that a possibility? You left other boyfriends in the past because you wanted to “be free and live the single life.” Is it possible that’s what you still want? Is it possible you keep looking for reasons to dump anyone who shows interest in you — even acting with “contempt,” as you say — because deep down what you really want is to be single and free? It’s worth thinking about.

Not everyone is meant to be paired up. Certainly, not everyone is meant to be paired up for the sake of being in a relationship. THAT is when you’re settling — when you commit to someone simply because it’s what you think you should be doing because it’s what everyone else is doing and it’s what society says is the normal thing to do.

What if… what if you remained single indefinitely? What if you kept dating around, but you gave yourself permission to not commit to any one person, to not call anyone your “boyfriend” and have all the strings that are attached to that title? You could still have the fun and companionship and affection without the pressure of being 100% compatible forever and ever. I wonder if that might free you up to enjoy and appreciate what a man can offer you without ticking boxes and comparing him to all the past boyfriends you left behind.

Rather than tell yourself you gave up pretty to settle for average, you could reframe it: You gave up the pressure of a committed relationship for the freedom of living single indefinitely. If that still doesn’t feel right to you though, I would strongly urge you to get some perspective and re-prioritize what you’re looking for. Looks fade. Good personalities, shared values, and chemistry last a lot longer.


Follow along on Facebook, and Instagram.

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


  1. dinoceros says:

    So, a couple of thoughts. You knew what he looked like when you first started dating him, so I’m not sure why at five months in, it’s just now becoming an issue. This should have been something that you used to decide whether to start dating him at all.

    Aside from that, you seem to think that past you and current you are very different. Both yous seem very critical of other people and seem uninterested in doing the legwork it takes to decide what you want BEFORE you loop someone else into your mess. I think you should break up with your boyfriend. Not because he’s not attractive enough, but because you’re just going to create misery for him in the end by being embarrassed by him and thinking you can do better.

  2. I’m genuinely hoping this isn’t real, because LW, I would assume by 44 you would have more maturity than this. If looks are your number 1 priority right now, then look for good looking men (realizing you will likely not get the full package, he may not be rich/super tall/have an amazing personality/may have kids etc.) Because, from the sound of it, YOU are not the whole package. Believe it or not, looks are not the number one reason for men to pick a woman.
    I’m sure if you read this you’ll assume I’m a bitter hag, but I’m 32 and I’ve been told I’m very conventionally attractive. But I realized I was dating a lot of men where I was prioritizing their looks first and missing out on so much. I have always focused on building myself outside of my looks (I hope you are too, but you don’t mention anything else about yourself?) e.g. my career, volunteering, hobbies, travel. Finding a man who was compatible with me on those levels first and who I also found wildly attractive was great — but I couldn’t care less if anyone else thinks he’s hot. I care that they think we’re happy. It seems you care more about the STATUS of having a good looking partner than the day to day reality of a relationship (because you don’t mention having issues in bed with him, etc, just that you haven’t introduced him to people…perhaps out of embarassment?). Is dating “hot” guys a way to make yourself feel less insecure/do you tie your self worth to your ability to get men to want you? Or, if at 44, you have consistently moved away from relationships holding out for someone “better” you may have commitment issues (or as Wendy suggested, maybe you don’t need to be paired up at all!). Have you considered therapy? As for this guy — I think if you are having doubts about it this early in the game, move on. Work on yourself, because it seems there may be underlying issues.

  3. Bittergaymark says:

    Karma is a real bitch. As sometimes are certain LWs…

  4. Avatar photo juliecatharine says:

    If this LW is 44 and thinking she’ll “eventually age” she’s more than a bit off in her perception. Lady, you’re aging, it’s happening, right now, to you, to all of us. If your bliss is the singles bar life have at it but if you want more you have a lot of work to do. Anyone you date deserves to be viewed as a whole person–not just a series of boxes to check and a prop you use to impress your friends. It’s really sad that you’re in your mid 40s and acting like a mean girl in high school. You may want to consider that all those compliments on your looks have stunted you in a very serious, very detrimental manner.

  5. How is it that you don’t think you’re shallow? Your entire letter is about ranking people on attractiveness.

    By your own description:
    – you are confident (I’m with you so far)
    – you get a lot compliments on you looks and figure (great, you’re good looking)
    – you’ve been unfocused/selfish/immature
    – you’ve treated interested men with contempt

    …you sound like a nightmare.

    What steps have you taken to make sure you’re no longer unfocused, selfish, and immature? Because that is exactly how this letter reads. You’re still dreaming about casually bumping into one of your former boyfriends (unfocused). You’re obsessed with how being with him will be perceived (selfish). You’re only criterion for decided if you’re not settling is looks (immature).

    You list not a single quality that any other boyfriend had, other than good looks. You’re not hung up on one great guy that got away, you’re hung up on literally anyone else that can validate how good looking you are by being good looking themselves.

    You say, “I can’t believe I dumped them. I guess a relationship wasn’t so important back then.” Do you really think you can have a quality relationship with literally any guy who’s interested as long as he’s handsome enough?

    You’re an actual person with interests and flaws and personality quirks, all completely aside from being really, really ridiculously good looking. I think you need a more solid understanding of yourself before you can pursue a serious relationship with anyone. Right now you’re too focused on looks and perception. Let this guy go before he finds out how embarrassed you are of his face.

    1. artsygirl says:

      Like the Zoolander quote!

  6. “I was unfocused/selfish/immature.”

    Guess what, you still are. I think at the root of it, you are tremendously insecure and depend upon constant compliments from men about your physical beauty to boost your self-esteem. You’re growing older and at age 44 the appearances of aging start to accelerate. As a well-beyond-70, I can assure you that is true for both men and women. So, those former bfs who were hotter than your current bf — they may not be as hot any more.

    Wouldn’t it be nice to be loved and admired for something other than your looks? Something that lasts a lifetime: character, personality, intelligence, empathy, achievements and activities are longer lasting sources of regard. Do you find yourself to be lacking in these areas and seek refuge in your looks? Do you project your shallowness onto the men around you and simply assume they can’t see anything about you, apart from your looks.

    Btw, looks don’t even make a great lover. Libido, openness, personality, empathy, sense of adventure are all more important.

  7. RedroverRedrover says:

    Read this:

    That’s you. You phrased it a little better, maybe. At least you sound like you actually like the guy. But essentially, you’re saying the same thing as that dude. Maybe you’re a little different in that you’d be ok with his looks if you thought your acquaintances wouldn’t care, but I honestly don’t know if that’s better or worse. Which is worse – to think you “deserve” someone hotter, or to want someone hotter because of what your friends and family will think? Both pretty messed up, IMO.

    My answer would be the same as to that guy – if you’re not happy, break up. The guy isn’t going to become magically better looking. If you’re so hung up on looks, let the poor bastard go and find someone who appreciates him.

    1. Red, I was thinking of precisely this guy when I read this letter! Wendy, do you still have his email? You can pass it along to today’s LW. Maybe they have time to do us all a favor and make the world’s most beautiful baby before her ovaries are kaput. Amirite?!

    2. I thought of this letter as I was reading, too, and how these two LWs deserve one another.

  8. I’m going to say (and really I’m not trolling) break up with Mike if he’s not good looking enough for you. If you feel like you’re settling you’ll be unhappy and he’ll be unhappy. I don’t think that it’s wrong for a woman or a man to say “these are my standards for being happy in a romantic relationship and I’m willing to be alone rather than give them up.” There’s someone out there who thinks Mike is great and he should be with that person.

    FWIW, it’s been my experience that when people say they receive “a lot of compliments” about their appearance and are often told that people mistake them for someone younger, they are confusing kind comments for a real, widely held opinion.

    1. You certainly weren’t trolling.

      Yes, it’s fine to have standards and stick to them, unto risk of being alone. But… it isn’t alright to date a guy for 5 months, when it is obvious from day 1 that he fails to meet the only standard that you truly care about. That’s wasting his time and hurting him, unless you made clear from the beginning that this possible relationship couldn’t possibly develop into anything.

  9. This hits on so many weird PUA/MRA notes that I almost think it has to be a troll email.

    1. This was my vibe as well.

    2. Yeah this has my vote. The LW is asking “I’ve written an incredibly shallow letter… Do you think I’m shallow?”

    3. Yep. The only thing missing is a mention of the “wall” or the “carousel.” This is a popular MRA fantasy.

  10. Avatar photo Skyblossom says:

    This is why I praise my daughter for her accomplishments and not her looks. She is very pretty but I give her compliments on what she does. We’ve also always emphasized valuing people for who they are and not caring about the cost of their home, the brands they wear, the cars they drive, their physical attractiveness or what career they may have. We value people for being good people and for being fun people and for being a good match to ourselves. We don’t worry about whether we will look good together. I can’t imagine meeting a friend and wondering if they look good enough for me to be seen with them. I can’t imagine focusing my friendships on something so shallow. I’ve encouraged my daughter and my son to base friendships on how the friend treats you with the expectation that you always treat the friend well.

    This LW would only be this uncomfortable about taking this guy home if her family has always made a point of putting looks ahead of everything and she has internalized that value. In her eyes and theirs she will devalue herself if she isn’t seen with a good enough looking man. Unfortunately, it can be hard to break over 40 years of ingrained judgement and she probably knows her family well enough to know their reaction. She needs to break away from their way of placing value on people but if she hasn’t done that by her mid 40s she isn’t likely to do that ever.

  11. Wow…I am with bgm again on this one.
    And I get the feeling LW isn’t as good looking as she thinks she is. (I know a woman around the same age who thinks she is gods gift and she isn’t very pretty at all! She gets attention from men more because of her aloff attitude and over confidence which attracts some people) She should stop seeing this guy and give him the chance to find someone worthy. He isn’t for her, I don’t think anyone is.
    This woman is in for a rude awakening because even Liz Taylor lost her looks. It happens to everyone . Reminds me of that episode of Tales From The Crypt “Only Skin Deep” with Lea Thompson.

  12. Northern Star says:

    Either this letter is fake (fingers crossed) or the LW is narcissistic to the point of ridiculousness.


  13. Why did you even go on date #1 with him if you weren’t attracted to him? Or you are plenty attracted to him but want your friends to think you have the best looking boyfriend.

    I have dated very handsome men, bald men, fat men, short men, tall men (seriously one was 6’8″, I never even saw him haha). I of course was attracted to all of them but that wasn’t just because they looked a certain way it was due to their personalities. Being good looking only lasts so long. One day those washboard abs soften and the Andy Garcia dark hair goes grey.

    This man deserves better than you.

    1. RedRoverRedRover says:

      This is a really good point. I guess my husband isn’t going to become a Calvin Klein underwear model anytime soon. Maybe most women would consider him to be only average-looking. But I really have no idea how other people see him, because I can only see him as what I see – a man I’m attracted to. To me, he’s attractive, and that doesn’t change based on other peoples’ opinions.

      So forget about what other people think. What do YOU see when you look at him? My guess is that you don’t find him attractive either, because if you did think he was attractive, I don’t think you could be so sure that your friends and family would find him average. Lesson learned – don’t date people that you, personally, do not find attractive.

      1. dinoceros says:

        Yeah, I’ve never been concerned about if my family and friends find someone attractive or not. My friends don’t care either. It’s not their boyfriend, so I don’t know why they would be concerned with whether he met their standards or not.

  14. Leslie Joan says:

    LW, you think you are interested in a relationship, but you really aren’t. You have always found a reason to break up with a guy, and lo and behold, you are still doing it. In other news, the sun continues to rise in the east every morning, just as it has for millenia.

    You are 44 years old and you’ve never really had a serious long term relationship. It’s abundantly clear to anyone on the outside looking in that you didn’t want one in the past, and that nothing is different now, even though you’re telling yourself that you’re ready for a relationship and have yourself a lil checklist. If you’d actually have been in one or more serious long term relationships before now, you’d understand that just because you might think you were oh so compatible with some of your previous dumpees, you really have no idea. That’s something you find out in the course of a relationship, not by consulting a checklist.

    I once dated someone who was in his late 40s who hadn’t ever had a relationship that lasted longer than 6 months. Ours lasted 9, which I suppose could have seemed a victory of sorts, but it was really clear to me by the end of it that there was a reason he couldn’t have a longer relationship, and it had to do with him. You are that guy. You will always find a reason to break up with someone, because for whatever reason inside of you, you’re terrified of a relationship and you’re looking for an excuse to run away. But you can’t run away from yourself. Therapy, for you, if you want to get a grip on what is driving you; or just keep dating and stay free. You will clearly dump this current fella regardless, so he is toast, but it’s optional for you to break your decades long pattern. Just don’t make it about his looks when it’s really about your own fears. Because if he were gorgeous, you would bbe finding another reason.

  15. I really hate people who think like this. If you’re not able to see a guy for who he is and how he treats you, and let THAT be what attracts you… you’re not ready for a serious, adult relationship.

  16. LW, I think a lot depends on why you want to be in a relationship.

    Is it because you want someone you can show off like a possession, to impress friends and family? Someone to prop up your self-image? Then yes, appearances are everything, and you should dump this guy. Find someone who’ll wow your friends. He should probably have a big bank account, too, for maximum effect.

    If you want to be in a relationship because you want love, companionship, a deep emotional connection, real intimacy, someone to grow old with, someone to have your back (and you have his)…well, I didn’t see anything in your letter indicating that you were interested in any of that. But if you are, then stop dating and start therapy, because you need a major, major change in the way you view yourself and other people.

  17. LisforLeslie says:

    Let’s say you’re dating someone down right gorgeous. If, for some reason, they get sick and don’t look good anymore – are you out the door? What happens if your personal George Clooney gets skin cancer and has to have a big old chunk of his forehead removed – are you out the door because your friends will cluck and say “Oh my, and he used to be so handsome!”?

    I think I know the answer and damn, you are one shallow person.

  18. He sounds like a nice guy and a great catch. Please let him go so he can find someone who isn’t going to dump on him down the line.

  19. oh girl- get over yourself. you are one shallow person. looks change. my sexy as hell hubby has gained over 60 pounds since we have been together. I have scars from surgeries . we are 50 and 56- I’m older. He still loves this scarred, flabby body. by the way- when I met him almost 25 years ago- he looked like a cross between Parker stevenson and alec baldwin- only better looking. any one my age will know. my parents were together over 50 years- my dad nursed my mom through 4 pregnancies, 2 open heart surgeries, many other procedures- she was always the most beautiful woman-she was inside and outside. Beauty is as beauty does. beauty is more than looks.

  20. I am constantly worried my boyfriend will find me less attractive as I age. He’s worried I’ll find him less attractive as he gains weight. His personality keeps me coming back, and I think he’s a stud. I see myself just getting more and more attracted to him over time. I just tell him I want his heart healthy.

  21. No offense LW, but you *do* realize you’re 44 and barring cosmetic surgery or other heroic efforts, you aren’t going to be such a great ‘catch’ yourself in a few years? I mean, you do get the concept that there’s more to a person than looks – such as kindness, intelligence, consideration, and some other pretty important traits it sounds like this guy has? I’m just thinking that you may have spent too much time around all those shallow, empty-headed hunks you used to treat with such disdain…..you might just not recognize a decent guy when you stumble over him.

  22. Purplestar says:

    Soon, if not already, people will begin saying “She is really attractive for her age”. This usually means that you are well groomed, smell good, and are not a hot mess. It does not mean that you have timeless, Aphrodite good looks. It is a nicety when they say that about you. It does not mean that you are are freakishly haggish, it just means you are aging along with the rest of us.

    I have found, as I have aged (52) that I get a lot of “You look great {for your age}” comments. And you know what, that is okay. I take care of myself and I am comfortable with my body – more so now than any other time in my life.

    As I got older, conversation, intelligence, stability, became more important than Adonis good looks. I met so many more interesting men. Ones I could talk to for hours. And the more intellectual stimulation there was – the more attractive these “average” looking men became. Wit and verve are very attractive and sexy.

    You say “Mike is smart, has a good personality, and is very open. He ticks most of the boxes”.

    If you can’t see past his “average” looks please break up with him. There are many women who would be proud to be with him. Don’t string him along. Just let him go. Give him my number. I love a smart man.

  23. Morecoffeeplease says:

    This seriously can’t be real, can it? LW, you sound so shallow and like you are someone who is insecure if you are not in a relationship. I suggest going to therapy to work on these issues you have. Why are you so focused on looks? Why is that so important to you? Why do you judge guys by how good looking they are? Why do you compare your looks to your boyfriends? What is this obsession you have with outer beauty? Please start going to a therapist because you sound really messed up.

  24. It is important to be attracted to your partner. He just isn’t doing it for you and I suspect that isn’t just about looks, but at 44 and single you may be avoidant. I found the response harsh, actually because I suspect there’s something wrong (avoidance is often the result of a difficult upbringing). Just as an aside, men are absolutely preoccupied with looks, I don’t think the response would have been as harsh with a male letter writer.

  25. There will be someone out there who will think Mike is the most handsome man on the planet, alongside his other many good qualities. Please do the guy a favour and break up with him so he’s free to date someone who’s genuinely attracted to him. He deserves that at least.

  26. Pinky Tuscadero says:

    Sounds like he’s too good for you. You are very shallow.

  27. LW….i think part of any relationship is being physically attracted to someone….the early stages of most (if not all) relationships are likely based on more physical attributes….it takes time to really get to know someone on a deeper level and see if there is chemistry between you to keep going long term….I think your feelings are totally normal….there are lots of nice people out there that we form connections to that can turn into lifelong friends….maybe that is what this boyfriend will turn out to be….we can’t help what we are attracted to and we can’t force it….there is no shame in admitting that you don’t find your boyfriend physically attractive….you just need to decide if you want to stay with him or find someone else who you are attracted to both physically and emotionally….that would also let your boyfriend have the opportunity to meet someone who may find him attractive….i hope things work out the way you want

Leave a Reply

Your email address will not be published. Required fields are marked *