“I’m Dating a Guy Who Isn’t Pretty Enough”

I am 27 years old and had a serious relationship two years ago, which was my first true love experience. There were certain issues he and I didn’t agree on, like values and beliefs, so, unfortunately, we had to leave each other. Half a year after our break up I tried to call him back and fix things with him, but he said he is not interested and he is in a different place now. I know his real reason was that he knew we wouldn’t be happy together and that getting back together wouldn’t solve our issues. Even though two years have passed, sometimes I feel I haven’t gotten over him yet. I go on dates, but at the end, when things don’t work with other guys, I always end up thinking about him.

Now I’m dating a 39-year-old guy; he was married in his twenties for one year, things didn’t work out for them, and he got divorced. I like his way of thinking and the way he sees the world, and I have a great respect for him. The two problems are: I think he is not a good looking guy — he has an attractive body but not a pretty face. The other thing that I find myself thinking about is that he is just finishing graduate school and works a temporary, part-time student’s job. When I told my friend about that, she told me that she thinks it’s not a good sign and that he should’ve been in a better place by now because he is not that young anymore.

I am really confused because I can feel that he is a good man, has a strong character, is very committed, and is not shallow. However, I can’t avoid thinking about the things I just wrote. I feel that a serious relationship can really do me good now. I badly need someone in my life. I would appreciate your advice on this! — Looking for a Pretty Face

You don’t “badly need someone in your life” right now. You’re just lonely, bored, and unfulfilled, and I know that because two years after breaking up with someone you didn’t share values or beliefs with, you think you aren’t over him and always end up thinking about him after ending things with other guys who aren’t right with you. That is classic behavior of someone who feels empty and bored and lonely and unfulfilled. You’ve convinced yourself that the answer to these problems is finding Mr. Right, and that couldn’t be more wrong.

As long as you are unhappy with yourself and your life, you will be a bad partner for someone else and you will fail at finding a fulfilling and satisfying relationship. You have to create the kind of life you’re happy in before you can invite someone else to share and expand it. If YOU’RE bored with yourself and your life, how is anyone else going to be excited? You’d be doing yourself, and especially this new guy who isn’t pretty, a real solid by moving on and focusing instead on bettering yourself. Because, honestly, a guy who almost has a graduate degree and has solid relationship experience, strong character, a good sense of commitment, AND an attractive body sounds like a great catch, and he is probably too good for some young woman with almost zero relationship experience who can’t get over some boyfriend from two years ago and who seems to have so little going for her that she’s obsessed with finding a boyfriend just to have SOMETHING to call her own.

Get some hobbies, take some classes, do some volunteer work, invest in yourself, invest in your community, invest in the environment — focus your energy really on anything other than finding a boyfriend, which is a pretty boring pursuit, and I think you’ll not only meet more people with whom you share common interests, but also you’ll attract higher quality men with whom you might eventually be able to build friendships and real relationships.


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


  1. Avatar photo Cleopatra Jones says:

    Oy vey. It’s going to be that kind of Friday. 🙁

    LW #1: EVERYTHING that Wendy said! Read it then re-read until you can recite it verbatim. Take it from someone with relationship experience, looking good is meaningless over the long term. Focus on how someone makes you feel AND how you feel in the relationship. You could be with someone who’s gorgeous as heck but makes you feel like shit being in a relationship with them. What happens if the person is no longer gorgeous? Do you dump him? And your friend is a shallow idiot, get better friends.

    LW #2 & 3: WWS!

  2. I don’t see how Wendy could have missed the larger issue in the last letter. As a therapist she obviously knew the importance of working through the big issues prior to marriage. That’s why they spent so much time working to bridge the huge gap between the total incompatibility of a Scorpius and a Sagitarius. She’s just asking you to suggest a solution to the smallish issue of a 180-degree dug-in difference on career and child-care. Did she forget to mention that she is actually an astrological counselor and that her husband laughs so hard he throws up in his mouth when she discusses this. “Shouldn’t we be discussing kids, where we’ll live, finances…” “No John, stick to the important stuff, our zodiac signs are incompatible, but….love!”

    1. 100% agree with Ron, definitely dropped the ball on this one Wendy 😉

      1. Gail Auth says:

        #whatwendysaid. Over, and over, and over.

  3. Anon from LA says:

    #1: I’m also a woman who values a pretty face, so I kinda get it.

    But… from the tone, it sounds like maybe the LW is looking for something wrong in her new BF, some way in which he doesn’t measure up to the ex.

  4. LW1: WWS

    LW2: I was lucky enough to stay home with our babies until the youngest was two. Then my ex and I worked opposite shifts for years and relied on limited interim care from family members for our daughters. It was tough but we really didn’t want to do the whole day care scene for various personal reasons. It worked pretty well.

    Your job sounds like it could be flexible – have you thought about a non-traditional schedule for yourself or your husband? I totally agree with Wendy that this should have been a pre-marriage conversation.

    And I have a question: you’re a therapist and you believe in astrology?

  5. Obviously that was meant for LW3 not 2. Gotcdo bored by LW1, I immediately forgot her.

  6. I am amazed an actual therapist thinks her and her husbands main incompatibility is their astrological signs. These are things you discuss before marriage. What about a compromise. You stay home, or he does for a year or two while the child is very young and daycare later. Many people do this as infant daycare is far more expensive and many want to be around for the breastfeeding, major development milestones that happen at this young age.

  7. Northern Star says:

    LW 3, I think it would be wise for you to quit your job and stay home with your baby. That way, people looking for a competent therapist aren’t meeting with someone who thinks freakin’ ASTROLOGICAL SIGNS are compatibility markers. GOOD LORD.

    1. Please don’t do this. There are enough idiots breeding as it is. I’m sure the stars would tell you the same.

  8. LW2: WWS. Also, buy a move-in ready house. Kids take up so much freaking time and money, and you won’t have any time for building or renovating a house. My husband and I have a 3 month old AND are trying to reno our bathroom (which was supposed to be done before I gave birth) and have almost no time to work on it due to jobs and baby. Save yourselves the headaches.

  9. If I found out my therapist believed in astrology I’d be out of there so quickly…

    1. anonymousse says:

      Well, is every planet in retrograde right now? That explains a lot.

  10. anonymousse says:

    Everyone needs to SLOW DOWN and think about things. JFC.

    LW1: you are lonely, shallow and not in a good place to be a good partner. Do what Wendy suggested.

    LW2: If a builder is telling you that you can’t afford it, you can’t afford it. Renovating while having a pregnancy and a newborn sounds like a nightmare as well. Save up. Sell the land, maybe. Regardless, it’s not the time to start a giant project. Maybe you can buy or rent a bigger apartment, condo, townhome, house, etc. Compromise. That, communication and good sex are kind of the fundamentals of a good long lasting relationship. If you can’t agree on where or how to live, how do you expect to have a child together?

    LW3: These are all things that probably should have been discussed BEFORE you got married. Regardless of your astrological signs- If you and he can not compromise, there is no other alternative. Split up before you have a child with a man you can’t come to an agreement with. You first paragraph says it all….if it takes that much work to make a relationship work…it’s not. Working, that is.

    Take it easy and slow down. Haste makes waste.

  11. The way he wrote the paragraph messes the wording, but he was stating that his WIFE doesn’t think they can afford it, not the builder (which without a comma makes it seem like it is a female builder saying they can’t afford it). He then states that he has shown his wife they can afford it.

    1. anonymousse says:

      They probably can not afford it. Otherwise, why would he have waited?
      Unexpected issues with giant price tags come up with building. Add lakefront property and I’m sure the unexpected permit issues, flood zone whatever…. it doesn’t sound like a sure thing.

    2. dinoceros says:

      Affordability is pretty subjective. It’s not just whether your income is more than your expenses.

      Take a couple deciding if they can afford a new car or not. Sure, they can probably pay all the payments. But does it mean they go without something else? Does it mean that they have no buffer in case an emergency happens? Does it mean that it only works if the car doesn’t have any maintenance issues? Does it mean that they can’t actually afford the insurance or gas for it? One person could easily “show” how it’s affordable (“Look, our remaining income after bills is more than the payment each month!”), but the other person could say it isn’t affordable due to the previously mentioned reasons, and they’d also be right.

      1. anonymousse says:

        Yeah, I think unless you have a sizable emergency fund, and all your bills paid in time, no giant outstanding debt…you can’t afford it. We are a country that has bought the “you deserve it” line. Hardly anyone makes large purchases with cold hard cash anymore, we all buy on credit.
        If his wife or the builder is saying he can’t afford it, and they have a baby on the way (even with insurance, birthing a child is expensive!) it’s probably not a question of can they, but rather should they?

  12. LW1: I find it courageous to study late and have a job to afford the study. You are very easily influenced, so I hope I put a little bit more value in your boyfriend. Too bad you don’t see it.
    LW2: you speak as if having a child and get married were such a disaster you need therapy to get over it. It had me laugh somehow. Those are happy events, enjoy! You both seem to rigid in your projects. Wendy is right: wait and spare. Your wife has a specific interest in a specific old house to renovate (this can be a bottomless pit financially speaking), or is this just a dream of hers? For while, you can just build small, for your week-end or vacations. If the builder warns you, then you are too short of money, believe her. Do it step by step, and enjoy the present, what you have, not what you wish you had.

  13. LW1…Even the prettiest people end up kinda ugly in the end. I have run into guys I used to think were so attractive. Now they have lost their hair, are a bit wrinkly and have a paunch. Lol Everyone gets older and age isn’t kind.
    I’ll bet letterwriter isn’t as pretty as she thinks she is either 😉
    LW2… You should slow down and sit tight for now. You probably feel in a hurry because you have a baby coming. Chill and enjoy your baby. Revisit the issue later. If you can afford your current living arrangement (and the mortgage on your property) there is no reason to rush. Kinda stupid to be on the brink of divorce over this. Geez!
    LW3- I love astrology, but a therapist basing her relationships on astrology? That’s a bit much. Is she for real? If she is a actually a real therapist, can’t she work part time? I know several therapists that have very flexible schedules.

  14. I find that my opinion of someone’s physical attraction can change when I get to know them. I’ve met guys with pretty faces who seemed less physically appealing once they revealed their inner ugliness. I’ve also met men I didn’t initially find attractive, and even in one case found decidedly unattractive, who I eventually started thinking of as good-looking because their beautiful characters shone through.

    LW1 sounds like she’s landed quite a catch. I hope she throws him back so that he can find someone who appreciates him just as he is.

  15. Autumnrose says:

    LW2 – congrats on buying lake front property. That is a great investment. I would just hang tight and no, not sell your property. If you are not hurting for money and can support your family than do not do that. I know you were trying to be an honorable man by marrying your pregnant lady but you shouldnt have rushed into something like marriage without clear understanding of what each of you want. You can always put a trailer on the property and build over time. You get your dream property and she gets her dream house…. Win win!! And congrats on your baby too!!

  16. Sandra Madera says:

    LW2: What about putting a pre-fab on your land? The biggest issue is they don’t give loans for pre-fabs, but if you’re not in a hurry to leave the apartment, perhaps you have time to save up.

  17. mellanthe says:

    LW1 – It’s unclear if this person actually fancies their partner. Because if they did, then it would be irrelevant. It seems like they’re looking for a partner to tick a box, and looking for people that meet all the criteria they think other people want.

    Because looks are meaningless if you like someone; your partner doesn’t have to be remotely conventionally attractive – they don’t have to appeal to anyone but you. I have no idea if my boyfriend is conventionally attractive. Obviously, I think he’s hot, but realistically speaking I’d say he was average? I like the little scar on his face, the slight gap in his teeth, his mannerisms his weirdly large hands (OK, he’s just tall in general) and his dadbod. Yes, some of those things aren’t conventionally attractive, but I find them endearing. What I’m trying to say is that you like about someone might not be conventionally attractive.

    I have a friend who’s like this- always showing me pictures of her friends’ boyfriends and criticising their looks. She even summed up the most recent guy she was seeing as ‘the least attractive man I’ve dated’ whilst she was seeing him. I think it can stem from insecurity- not wanting to be seen with someone others might find less desirable. But if you love someone you couldn’t care less what others think of their looks. They won’t be the ones sleeping with them after all.

  18. Anonymous says:

    Either you’re looking for some exscuse to break up with every good guy you meet, or he really is a Shrek. Don’t listen to other people. It’s perfectly ok to break up because you aren’t attracted enough to them. Often times you can’t even control your attractions. Let alone dismantle them.

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