“I Find Flaws in Every Woman I Date”

I’m 42 years of age and have never married. Although I have had a few successful stints with women, I ALWAYS find a flaw in my partner. It is a real problem for me. It started in college. I would always have certain girls I was very attracted to and would do anything to date. However, when they showed interest in me and we started to date, I suddenly found them less attractive. I am definitely attracted to women; I just constantly struggle to stay attracted to a woman for more than a month or two. I find ridiculous flaws like their chin, their eyes, their figure, their teeth and other minuscule things. The crazy thing is that I notice my flaws just as much. (I inherited terrible posture from my father.) I know that no one is perfect on the outside.

My most recent relationship was with “Sue.” She was attractive, but her chin was abnormally large and I couldn’t help but consistently notice it. She also bit her nails. I realize these are two small flaws, but for some reason they bothered me way too much to stay with her.

I really would like some advice on this. I want to find someone perfect for me, but I realize I have to reduce my definition of perfect. Please help me on how this could happen. — Searching For My Perfect

You know that everyone is flawed, and yet you end relationships over ridiculously superficial flaws that have nothing to do with who a person is, how she treats you, and what your relationship is or could be like. Dumping a woman because of the size of her chin? That’s pubescent behavior — not the act of a secure, mature 42-year-old man who is serious about finding a “perfect for him” match. YOU are the problem here. It’s YOUR flaws keeping you from having a relationship (and I’m not talking about your posture). Your flaw is your fear and until you name your fear — fear of commitment? intimacy? rejection? losing your identity as a bachelor? being beholden to someone else’s needs and wants? making the wrong choice? — and get to the root of its cause, you will never, ever find a perfect-for-you match, even if one exists.

You are looking for reasons to reject women, and instead of even bothering to get to know them as people, you are focusing on their physical traits (which is ironic, because all of us have plenty of character flaws and our own baggage that could rightfully give others pause before pursuing a serious relationship). That’s not just immature, it’s also lazy. And it’s not just doing these women a disservice, it’s doing a bigger disservice to yourself. The benefits of longterm relationships are numerous. What benefit do you get from rejecting potential relationships before they even begin? Maybe if you could name those benefits, as well as your fears, you’d finally get somewhere. I suggest doing so with a great therapist who can work with you through these questions and give you tools and exercises to help you name what you’re looking for and get you out of your own way in finding it.

I’m a 22-year-old female from Australia. One of my friends is planning a Contiki trip around Europe and I would love to go with her because I don’t have a full-time job I need to be at, I can afford it financially, and I would be finished with all of my university exams by the time I would go. But when I brought it up with my boyfriend, he told me that he hated the idea. Last year he went on a Contiki trip around Europe for six weeks with three of his friends, during which time one of his friends cheated on his girlfriend. My boyfriend remained faithful.

What I hate is the fact I’m only wanting to go for three weeks (instead of the six he went for), but he is being selfish and isn’t going to allow me to go with one of my friends. Should I book the trip despite his feelings and face the repercussions? Or should I just not go and let him get his way? — Three Weeks is Shorter Than Six

Pardon my French — a language you might be exposed to on your trip to Europe — but fuck that shit! Your boyfriend is a TOOL if he thinks he can forbid you to do anything, especially go on the same trip he took himself a year earlier. Methinks maybe he wasn’t as faithful as he claims he was or he wouldn’t be so afraid of the way you might behave on your trip. Projecting one’s own indiscretions onto others is a common trait among tools and fools. Don’t be conned by his lame game. MOA and go on your trip. Why just three weeks? Make it six and have a great time, You’re 22 and free. Live it up, girl! I’m sure your boyfriend did…

My husband and I were married for eleven years, have three kids together, and are in the middle of our divorce process. He started an affair in January, 2016. I found out in November. He stated he wanted to try and work things out, so I agreed. But he never stopped talking to the other woman and I couldn’t take the lies anymore, so I ended it. Now he calls and texts me at random times for random things. For example, last Wednesday he flew to Minnesota to see his chick. He texted me the day he left and let me know each of the three times he arrived at an airport. Then texted the next day saying he’d be calling our girls that night and saying he wanted to see how things were going. He did the same on Sunday, Monday, yesterday and today. He is flying home tonight. What is the purpose of these texts and calls? He claims he’s chosen to be with her, so why contact me even when home let alone with her?! — Soon-to-Be Ex-Wife

Because habits are hard to break, and ain’t no habit like an 11-year marriage. Plus, with three kids in the picture, he absolutely will always have a legit reason to be in touch with you about his plans and whereabouts. That doesn’t mean you need to know where he is at all times! Nor should you have to even give the illusion that his personal well-being is of such concern to you that you need to hear every time he arrives somewhere safely.

Make no mistake: His reaching out to you is about him — his comfort and his habits. It isn’t about wanting you back or having second thoughts about leaving you for another woman. He has chosen her. For over a year, he has chosen her. He left you and your kids and is pursuing another woman. So, be firm, and for the sake of your kids, be strong and civil. Tell him that you are moving on and for him to respect your moving on and to stop making unnecessary check-ins with you. Let him know that he’s welcome to talk to the kids at times that are convenient to you and them, but that if he continues sending random texts that have nothing to do with them, you will consider that harassment and will not tolerate that. If it continues, mention this to your divorce attorney and get legal advice for how best to handle it moving forward.


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@dearwendy.com.


  1. artsygirl says:

    LW1 – It sounds like you enjoy the chase and lead up to a relationship but have no interest in the relationship itself. Since you have obviously known about this problem for over two decades and not been able to overcome it, it is time to talk to a professional.

    LW2 – So your BF has so little trust in you that he thinks you will cheat? He claims he didn’t cheat so why does he think you will? Basically his behavior is controlling and unacceptable.

    LW3 – As Wendy said, set boundaries and maintain them. You can be civil but you should not have to deal with manipulative behavior. Best of luck

  2. LisforLeslie says:

    WWS on all three.

    LW1 – this is totally your issue. These women are perfect until you have a real shot with them. You know this is your issue. You need professional help to deal with it.

    LW2. Fuck. That. Shit.

    LW3 – if he won’t stop texting, do your best to ignore. Do not read into it. If he’s flying to meet the other chick and he’s telling you he’s at the airport – he is only telling you at the airport because he wants someone to know where he is and your’e the usual person after 11 years. There is likely nothing more behind it than that.

  3. findingtheearth says:

    LW1: I have yet to meet a single person without a flaw. Focusing on flaws or going searching for them is definitely a sign you need some sort of counseling if you are serious about finding a mate.

    LW2: go. This might be your only chance to make these plans and enjoy the time with your friend. Any mature and trusting boyfriend would recognize that.

    LW3: I agree with everyone that it is a force of habit and for comfort. You might just need to tell him that you don’t need the updates when he travels or on his daily routine. He should contact you regarding the children or other large life happenings that influence the children.

  4. AuntyMacasar says:

    LW2 – This has been said before, but I’d like to repeat with emphasis: You are an adult, and your partners do not have the right or the power to tell you what you can or cannot do. You should be especially wary of a partner who tries to interfere with your personal growth. Partners come and go, but the stuff you do for yourself is yours and yours alone.

  5. Anonymous says:

    LW1: Your definition of “perfect” is solely about physical characteristics. But when you get to know someone and care about her, slight physical imperfections become much less important. You will look at the person and see love, kindness, intelligence, joy—not the size of her chin. I hope you can find that out for yourself some day (follow Wendy’s advice and see a therapist).

  6. SpaceySteph says:

    LW1: I suspect you are focused on the flaws of others because you have some flaw of your own that you are very sensitive about and worry if a woman gets close to you she will dump you over it. We all have flaws and we all look past the flaws in others in order to have meaningful long-term relationships. We do it with our friends, with our families, and yes, with our lovers. So get out there and embrace that third nipple you’re so worried about, whether it be with big-chin-lady or someone else!

    LW2: Definitely GO! Before you know it you’ll be an old person like me with a full time job and a mortgage and a dog and a baby on the way and you won’t have time, funds, or energy to go on a trip like this. This guy you’re with at 22 may be the one you spend your life with, or he may not(If he really would stop you from going on this trip, I’m going to guess *not*), but the memories of that trip will last a lifetime! DO IT!

  7. LW1 – I think you need to ask yourself what you want from a relationship. Why do you want a partner. I think you need to work from that place then work outward. I think you are looking at the external and finding flaws but if you found someone who you truly connected with on a soul level, those flaws would be glazed over. This is a Dan Savage line but I love it. Every relationship has a cost of entry and you need to decide if someone is worth the cost. Whether it is physical or emotional or quirky. The girl with the chin and nails, other than that did she make you laugh, make you feel loved, make you want to sit at dinners for hours talking, love your weird collection or hobby? It might have been that there wasn’t much else there besides sex so it wasn’t worth the nail biting.

  8. LW1 I agree this sounds like a potential commitment issue, fear of rejection. Some sessions with a good therapist will help you get to the bottom of this. Trust me, it’s worth every minute and every penny.

    LW2 I agree your boyfriend is most likely projecting his indiscretions onto you. Or is just a ridiculously insecure person. Either way, ain’t nobody got time for that! Go on your trip. I have yet to regret any trips I’ve taken, but let me tell ya; I certainly regret passing up on cool excursion adventures. If he makes any more of a stink about you going, promptly dump his ass.

    LW3: It’s hard to tell what your ex’s intentions are here, but no matter what they are, stick to your guns. It doesn’t sound like you need help doing that though, good for you for acknowledging this madness and choosing to not get swept up in it!

  9. On LW #2 — or this very controlling guy could be a future abuser. This level of control is unhealthy. To ask should I go “and face the repercussions”, the answer is you should go and if there are repercussions you should immediately break up with him.

    1. ReadytoMingle says:

      Exactly. You are young. You will regret allowing someone else to ALLOW you to do anything. This is a person that will continue to control you. And I agree with those saying he is probably projecting his own behavior onto you. Take it from someone who was accused of being unfaithful for 20 years (I wasn’t) by someone who was. Go on your trip, come home and dump that guy.

  10. LW1: Yes to all that was said but the biting nails thing make me laugh out loud, at you. If chewing on a fingernail is a “flaw” then your standards are ridiculous. You sound pretty darn flawed yourself. A large chin isn’t a flaw, its a genetic characteristic. I truly wish we had your name so we could find a pic of you and point out that your hairline isn’t quite right and your nose is a bit large, etc. You sound like a jerk to me, I wouldn’t want to date you….and guess what, you are the age of men I date. Perhaps do these women a favor on the first date and show them this letter you wrote so they can see how flawed you are and MOA before they waste an ounce of energy.

  11. LW1: “Most married couples, even though they love each other very much in theory, tend to view each other in practice as large teeming flaw colonies…” – Dave Barry. This is one of my favourite quotes. Seriously, you should not date until you seek some sort of therapy. The position of “I’m hypercritical of everyone , but it’s OK because I’m equally hypercritical of myself” is one of the most self-defeating ideas ever. Being a dick to yourself doesn’t give you a free pass to be a dick to everyone else. You will never find any joy in a relationship until you deal with this problem in yourself. The flaws are the good stuff. The part nobody but you knows about. You are a witness to and a defender of the flawed but beautiful humanity of another person. That’s what love is.

    LW2: Yeah, I gave up pretty early on trying to forbid women from doing anything, because, like, it’s modern times, and they all told me to get stuffed. You should try that with your fella.

    LW3: I’m thinking “Get stuffed” works pretty well here too. You need to co-parent with your ex for the sake of the kids. The rest he can stick.

    1. SpaceySteph says:

      Diablo, that last part to LW1 is quite lovely. Perhaps that’s becoming one of my favorite quotes.

      And the rest of this is spot-on, too.

      1. Thanks, but like a lot of my wisdom, it is all stolen from the dialogue of great movies. “Flaws are the good stuff” comes from Robin Williams’ character in “Good Will Hunting.” Your partner being a witness to your life comes from Susan Sarandon’s character in the American remake of “Shall We Dance?” Under pressure, I have also been known to quote the lyrics of popular songs.

      2. LisforLeslie says:

        Ah Diablo, you don’t give yourself enough credit. My question to you: do you do this to your wife and how does she manage to keep herself from rolling her eyes too hard when she realizes you’re quoting another movie? 🙂

      3. @LforL – Sometimes we have entire conversations which consist of snippets of dialogue from various movies. To win, you have to find a clever segue from one scene to another that switches the tone of the conversation or argument to your point of view. Sometimes I’ll blow the whole thing up with Nicholas Cage from Moonstruck: “I don’t care!! i ain’t no freakin’ monument to JUSTICE!!!”

  12. LW1 – as someone who dated someone just like you, please get some therapy and focus on yourself for a while before you start wasting another person’s time, thinking that they are building a relationship with you.

    Signed, someone who wasted 2 years of my life with someone like you.

  13. dinoceros says:

    LW1: I’m going to give you the benefit of the doubt that you’re not that superficial and that maybe there’s something that scares you about being in a relationship, so you push people away instead of moving forward them. Perhaps some therapy might help?

    LW2: I’m disturbed that you think your boyfriend has the ability to allow or not allow you do something. He is not your owner. Anybody who is so insecure that they try to forbid you from traveling because they are afraid you will cheat doesn’t deserve to have a girlfriend.

    LW3: Tell him that you are not interested in getting texts from him unless it directly involves your kids. Ignore all texts that are about anything else.

  14. Avatar photo Skyblossom says:

    LW3 He may be trying to rub your nose in his relationship. Texting you at the airport, repeatedly, is certainly a way to make sure you know he is still seeing the other woman. It seems rude, like a little kid saying look at me and what I’ve got. I’d ignore his texts like they don’t exist so he quits getting whatever he gets out of sending them to you. People tend to do things because they get something out of it.

    1. Avatar photo Cleopatra Jones says:

      Agree. There is just something about his actions that scream, ‘Look, at me. I’ve moved on and you’re still alone!’ Ugh, so juvenile.

      I would seriously ignore any texts from him that weren’t about the kids. Don’t even respond because that will encourage him to find other stuff to pick at you about. If he calls, make sure the calls are about the kids, anything else means that you need to end the call now!

  15. LW 1. Is your name Frasier Crane by chance?

  16. LW2 – I just have to say that I did a Contiki tour with 5 of my friends after college. We did 3 weeks in Europe and it was amazing. We still talk about it, and I am so glad you did.

    Your boyfriend is not right to tell you he doesn’t want you to do. That’s his insecurity, and there is nothing wrong with going on a long trip with your friends without a significant other. Go with your friend, and HAVE FUN!

    Also, you should seriously evaluate your relationship. Is he jealous and controlling in other ways? If so, might be time to break it off and find someone who trusts you! I stayed in a jealous controlling relationship when I was younger for way too long. I really wish I had ended it sooner. And I found many a great, trusting guy after that one.

    Also, if you decide the relationship is unhealthy and you want to break up, do it before your trip so you can be single in Europe 😀

Leave a Reply

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