“What Can I Do To Make Him Love Me?”


There’s this man — let’s call him “Handsome” — whom I’ve been intimate with, on and off, for four years. He is going on 38, never had a girlfriend, yet claims to be “lonely” and self identifies as having “issues” when it comes to relationships. Whether this means he’s just a player, or actually desires more intimacy and vulnerability with a woman, remains a mystery.

Since I’ve known Handsome, I had a child with another man (whom I love deeply and dearly, but that’s another topic for another day). When my son was about 20 months, Handsome and I reconnected and it felt redemptive, like the reset we had both been seeking. Our balance was better — I feel redefined, more confident, and more complete as a person in his presence. He asked me, sitting on a Brooklyn rooftop, if I felt we had closure before. It had been over two years since I’d even communicated with him, let alone seen him. Until he asked the question, I thought there had been enough closure for me not to look back.

Since then, we’ve had a number of trysts — difficult to arrange (he works too much, making up for lost time after having been laid off and unemployed for a couple years, which really did damage to his ego; I have a kid) and while I started out feeling hopeful about our future, I feel old patterns of passive aggression (in his radio silence) and imbalance (my desire for him being insatiable) creeping in.

The rub is, I’ve cut things off with Handsome, clearly and painfully, two times in the past because I felt then I needed more from him. This time, I went in committed to being patient, loving, accepting, and open with him. After all, where am I going so fast? Nowhere, and I do get what I need sexually from him and only him. But I get so frustrated when he doesn’t ask me out, or doesn’t even communicate with me, and then I “jam it” by making arrangements for us and being persistent about it working out. He goes along with the plans and makes sacrifices, and claims to hate dating others. (As for my part, I HATE dating others, too — I want every date night to end in Handsome’s bed).

Is he just being lazy and selfish with me and giving into the convenience? Am I enabling this? What do I have to do on my part to give us a real shot at giving a relationship a go? Or is it doomed? Do I have to step back and create space for him to act? Do I have to say no? Do I have to date others? What signs should I look for him in him or questions should I ask to know if our relationship means anything lasting to him?

And finally, why can’t I just be Lena Olin’s character (Sabina) in the “Unbearable Lightness of Being,” wearing that sexy top hat and in control having a lifelong love affair with a man without wanting to possess him. In my dreams…

— Lustful and Lonely

I’ll answer your easiest questions first: yes, Handsome is being selfish and giving into the convenience of your availability and eagerness to be with him. Yes, you are enabling his behavior. And as for signs to look for to determine his level of commitment, I’d say they are pretty obvious if you simply pull your head out of the sand and look: he never makes plans with you; after being dumped by you twice before, he is STILL not putting any effort into keeping you around this time. It would seem that, yes, the relationship — at least the relationship you want with him — is probably doomed, I’m sorry to say.

I know how hard it can be to accept a reality you don’t want. But this IS reality. It’s not fiction and you aren’t a character in a novel or a film and the faster you embrace that and take some control of your own narrative the happier you will be in the long run. Think about it: you are a grown woman — with a child! — and you are waiting for someone else — someone who has a history of disappointing you — to give you what you want. And while you wait — indefinitely, it seems — taking whatever crumbs he offers you, you are potentially missing out on other story lines — personal narratives that could make you much happier than your current one. Because while it’s nice that Handsome fulfills your sexual needs, it’s quite obvious that those are the ONLY needs he seems to be fulfilling. And not only is he not fulfilling other needs, he’s likely depleting your reserves of patience and love and, frankly, happiness. How much disappointment will you put up with before you’re ready to MOA?

I’d be curious to hear the story of your child’s father. If you love him deeply and dearly, is he someone who could fulfill your desire for companionship and true partnership? If not, then I’d suggest cleaning the slate and starting fresh. Handsome may occasionally keep you warm on cold nights — when it’s convenient for him, of course — and I’m sure, as a single mother, you find that especially welcome. But he will leave you cold more often than not. And worse, he will leave you feeling like you’ve done something wrong or that, if you only knew the right words or the right moves, you could make him be the kind of partner you crave. But you can’t. Because this is real life and the only person whose behavior you can control is your own. So take some control and decide that starting now you won’t accept less than what you truly want in a relationship. The only kind of “possession” that I’d call that is self-possession, and that’s the best kind to have.


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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. OP, you won’t last long. I knew a guy like “Handsome” – things seemed to fall into place when he was around. But getting him around was a hassle, and I felt taken for granted, and so I bolted.

    Anyway, I’m only commenting to say that you write beautifully and I enjoyed reading your letter. Hope you’ll write some more!

  2. LW, it seems to me that all the layers of complication you’ve added to this story – all the stuff about closure, vulnerability, him having issues – are just there to cover up the simplicity of the fact that Handsome is just not that into you. Some things really are simple: If he really wanted to be with you, he could and would. And honestly, I think pining after someone for years and years is a bad look on anyone, but much more so on a grown woman with a child. You’re missing out on so much by investing yourself in this love affair.

    1. That’s exactly what I was thinking. LW writes all of this flowery language and try to spin this narrative into something out of a romance novel. After reading the letter all I could think of was… that’s it? This guy has a nice convenient booty call and she wants to know if it can be something more?

      The answer is no. If he wanted to be something with her he would have made it happen. People who REALLY want things will not wait (for several years no less!).

      I understand how easy it is to let yourself fall into this trap. But once she finds someone who really wants to be with her and proves that he does by putting forth an effort, than she’ll wonder what she was doing with this guy in the first place.

      1. I totally agree with this… Unfortunately I feel like this LW has spun this elaborate romance fantasy out in her head and somewhat into her life. That sucks and I hope she starts a new chapter taken care of business for herself and her child, without ‘Handsome’.

      2. zombeyonce says:

        I agree that she should start a new chapter mainly thinking about herself and her child.

        I’m relieved this letter didn’t include the always sad line, “He’s so great with my kid!” It seems to show up in a lot of letters from single mothers and I always feel bad for the child. I’m glad LW didn’t do this.

    2. +1000. All I could think the whole time I read this was “he’s just not that into you!!!!!” If this letter is even real, which … I have my doubts. Like Heather said, it screams undergrad creative writing seminar with the Brooklyn rooftop and Handsome and Lena Olin stuff.

  3. before i even read it- no, there is nothing you can do to make him love you.

    after reading it- so dramatic, LW! wow. real life isnt like that. well, i mean, i guess yours is, but it doesnt have to be… and since you seem unhappy about the whole thing, id change something.

  4. Bittergaymark says:

    Ugh. Grow the fuck up and raise your child. When your romantic role model is a mediocre actress (at best) in a so-so film few have seen — eh, it’s high time to simply give your warped version of dating a good long rest.

    1. ugh i thought this letter was fake, I mean are there people out there actually like this? I guess I just don’t know anyone who writes or thinks like this…(I saw others say it was beautiful…I found it completely cringe worthy both for its content and style) The time for you to quit fantasizing about this man was roughly when you expelled another human from your body. Being dreamy, self absorbed, and using artsy-fartsy movies to illustrate your point is only acceptable in your twenties. You are not twenty. Grow UP!

  5. LW, you sound like a 15 year old girl in this letter. Really, you do. This guy doesn’t want to have a relationship with you. At least not the kind you want. You can’t say or do anything to make him love you.

    Stop waiting around for this guy, and focus on your child. Be a mature, reasonable role model for your son.

  6. Lily in NYC says:

    I feel like I just watched an episode of that stupid “Girls” show. But honestly OP, it’s too late for you and Handsome. He’s dysfunctional and you’ve made it way too easy for him from the start by coddling his emotional crap. I get the feeling this guy needs a more dominant type of partner – one who actually ISN’T understanding or patient (my mom would be perfect for him, lol). The dynamic you guys have just doesn’t work. You need to cut him out of your life oompletely; it sounds like you get angry with yourself when you settle for crumbs with this guy.

  7. AliceInDairyland says:


    What kind of movie is this?!?!?! Why is this being idolized…?!?!?! Do what you want to do, but this plot seems so confusing…

    1. geez seriously? wow. what a trainwreck of lives.

    2. Avatar photo muchachaenlaventana says:

      It was actually a book first, by Milan Kundera and yes it is highly confusing but enjoyable and presents a pretty interesting view on things. It is a weird book though and a really strange one for someone to idolize that character from.

    3. Avatar photo GatorGirl says:

      I can’t even get through the first paragraph of that plot summary….FFS.

      Also…sexy top hat? What??

      1. ahh the top hat scene (in the book). you’ll have to read it to understand it

      2. Avatar photo GatorGirl says:

        I started googling, it sounds like it’s a bowler hat from someone grandfather? I just don’t think this is a story for me.

      3. From the book: “When we want to give expression to a dramatic situation in our lives, we tend to use metaphors of heaviness. We say that something has become a great burden to us. We either bear the burden or fail and go down with it, we struggle with it, win or lose. And Sabina-what had come over her? Nothing. She had left a man because she felt like leaving him. Had he persecuted her? Had he tried to take revenge on her? No. Her drama was a drama not of heaviness but of lightness. What fell to her lot was not the burden but the unbearable lightness of being.”

    4. Avatar photo GatorGirl says:

      I can’t even get through the first paragraph of that plot summary….FFS.

      Also…sexy top hat? What??

      1. Avatar photo Addie Pray says:

        I always wear sexy top hats whilst making sweet love. Not you?

      2. Avatar photo GatorGirl says:

        I can’t say a top hat has ever made it into my sexy time. Perhaps I should spice things up and add one.

      3. I actually do think top hats are sexy.

      4. Avatar photo GatorGirl says:

        really? Hmm. What ever floats your boat, it’s just never crossed my mind.

      5. Avatar photo GatorGirl says:

        Yeah, it makes sense in a burlesque kind of way (if that makes sense). I just go straight to Abraham Lincoln, and well he isn’t my cup of tea. (I probably spend too much time with history people.)

      6. You need to go straight to Mae West. Or Greta Garbo. Yum.

      7. Avatar photo GatorGirl says:

        Yeah…it’s just not my thing. I looked both of them up in top hats, and it’s just not attractive to me.

      8. I think Abe Lincoln is sexy, so maybe that’s my problem here. haha

      9. Me too! I was helping my friend take out the trash before a Halloween party, and it took all my willpower to not follow the guy in the parking lot dressed up like Abraham Lincoln.

    5. Sue Jones says:

      I liked the movie when it came out, but I was in my 20’s and it seemed SOOOOO romantic. SOOOO European…. Now I have no time for all of that drama and complication. See once you find a decent partner you actually get to focus on other more productive things in your life.

    6. Avatar photo Addie Pray says:

      Oh my gawd I have been trying to get through the book for years. But it’s impossible for me, on account of how god awful boring I find it. It should be renamed: “The Unbearable Lightness of Boredom.”

    7. the book is great… i don’t know about the film (i think daniel day lewis is in there).

      1. Sue Jones says:

        Daniel Day Lewis was indeed in the movie and he was SOOOOO HOT!!!! Juliette Binoche also. But I am so glad I the many I married is nothing like his character…

      2. Sue Jones says:

        “Man I married”, not “many I married”….

    8. the book is great but i haven’t seen the movie (i think daniel day lewis and juliette binoche are there)

    9. Avatar photo Astronomer says:

      It’s one of those books you have to read to “get,” if that makes sense. Like, the plot summary sounds kind of goofy, but the book itself is sexy and political and interesting. I agree that some of the moral complications of Tomas’ character are hard to stomach, but Sabina is one of the most compelling and not-tied-to-a-specific-man female characters of that time. She’s an interesting foil for Thereza, who is the “ideal” wife, but so simple and boring you almost want to cheat on her, too. I haven’t read it since I was 20ish, though, so take that opinion with a grain of salt.

      Also, I used to use Tomas’ “Take off your clothes” line on dates, and it always, always worked.

  8. starpattern says:

    LW, I feel like you’re looking to turn this into some epic, dramatic love story. It’s kind of hard (for me at least) to read through the fluffy language and get to the actual meat of the situation, which is… this guy likes you, but not enough to ditch his bachelor lifestyle and make you his first ever girlfriend. You know?

    Hold out for a guy who wants – really wants – to be with you. You may not have a dramatic story to tell about how you got together, but you will probably be much happier.

  9. tbrucemom says:

    Not to be crude, but it sounds like the baby daddy isn’t getting the job done in the bedroom to her satisfaction and the BF is rocking her world in it. I too am curious about her saying she loves the BD but crying over the other guy who frankly doesn’t sound like he’s worthy of anything but a good lay. I wonder if the BD wants to be with her and their child but he’s not giving him a chance because of her infatuation with the other guy. I really wish she would have given more details about that relationship. Bottom line is take care of your child first and stop living in a fantasy world.

  10. Avatar photo Addie Pray says:

    I love it when every sentence Wendy writes could just as easily end in “and that goes for you too, Addie Pray!” I mean, even when the letter is not exactly applicable, there’s always a take-away in the advice for me (and I’m sure for the rest of you too). That’s all. Happy Monday, everyone. I slept 8.5 hours on account of the Tylenol PM I took at 3:30 am, and I am one GROGGY happy camper this morning. My goal is to be productive at work this week. Wish me luck. Ciao!

  11. Wendy’s reply was so beautifully written & compassionate, I really liked it. Please listen to her, LW.

    This guy doesn’t want you the way you want him, & I’m sorry. A relationship involves both parties making plans, not one trying ~not~ to make plans, finally giving in with impatience once never hearing from the other party, & then being told by the other party that they’re “jamming” (?) things up by being “persistent”. I get it, right, this guy is free like a bird & you can’t cage or “possess” him, & you, LW, are wondering why you can’t just be cool & let him fly while carrying on a “lifelong love affair” with no expectations. Just like Sabrina or whatever character from whatever film you’re even talking about.

    Life doesn’t work like fiction, however, or your “dreams” (which, I’m glad for your last line because it indicates that you realize you’re being fantastical, here?). It’s okay to have a bit of romance in your life, & as much as I hate when LWs write in all flowery, I’ve been guilty of pretending to be a fictional character in my own life every now & then. But you need to get grounded, now, because you’re only being hurt by this situation.

  12. LW, the time for all of your tortured dating drama was before you had a child. Now you don’t have the luxury of having “a lifelong affair with a man without possessing him” or even chasing after one who doesn’t want to be with you, which is clearly what you’re doing here, romanticizing language or not. You’re not in an affair, you’re a FWB, at best. And that’s probably pushing it. So, just stop. For the sale of your child, stop. Put the energy you are currently putting into chasing a man who isn’t into you to better use by focusing on raising your child and working through why exactly it is that you are so enamored with a guy you know deep down you will never have and then, use that insight to fix your life. Are you afraid of commitment? Are you just bored? Do you feel stuck and this is a nice fantasy? Do you just have a very melodramatic view of dating? Whatever it is, work on that because spending your life chasing down the unavailable and/or unwilling is only going to leave you sad, alone and unfulfilled, and that’s terrible for both you and your child.

  13. Avatar photo lemongrass says:

    The men that you date and the way you allow men to treat you is what your son will grow up internalizing as normal adult behaviour. He will treat women that way. Are you okay with that? How would you feel to find out someday that your son is acting the way this guy is? Don’t accept any less from a man than how you want your son to grow up because you are his role model of how women are treated.

    1. Avatar photo shanshantastic says:

      So, so agreed. And it doesn’t matter how much you think you’re keeping him in the dark, LW – our children see so much more than we anticipate. Show him what kind of partner to be…and what kind of partner to seek. Good luck.

  14. Avatar photo landygirl says:

    LW, it seems as if you love the drama of it all. I’m guessing the baby’s daddy is either married or won’t commit to you. You choose men to further your dramatic narrative, meanwhile your poor baby will be at affect of your need for drama.

    Maybe you should seek therapy to figure out why you continually make poor choices for yourself. Yes, that statement is presumptuous but not as preposterous as your letter.

  15. The answer to to the question “What can I do to make him love me?” is always ‘nothing.’

  16. kerrycontrary says:

    This guy likes sleeping with you occasionally, when he can find the time, or when you make him find the time or track him down and convince him to sleep with you. Basically, he’s not that interested and doesn’t want a girlfriend, and certainly does not want YOU to be his girlfriend. More importantly, you don’t mention him showing any interest in being a step-parent(or what have you) to your child. Focus on co-parenting your child with your babydaddy and maybe someone will come along. But that someone is definitely not this guy.

  17. LW – it is said that the definition of insanity is doing the same thing over and over again and expecting a different result.

  18. findingtheearth says:

    Booty call. Plain and simple.

    If that’s all you want to be, then keep this going with him. If you want more, then find someone else. We only accept the love we think we deserve.

  19. stonegypsy says:

    This letter could seriously be about one of the guys I’m dating (aside from the age), the major difference being that I’m grounded enough in reality to not actually expect anything except occasional fun.
    It’s so easy to live in a fantasy world and imagine away all of the negative qualities of the person you’re infatuated with, but even if this guy did decide he was suddenly ready to settle down, he probably isn’t the perfect match for you that you imagine him to be. Cut off contact and stop letting him back into your life (I mean, theoretically you could keep him as a booty call but I think you’re too emotionally attached for that to work), and either be alone or date other people.

  20. Do you really want to be in a relationship with someone who has self-admitted relationship issues and was unemployed for “a couple of years”? Someone who consistently doesn’t give you enough? Someone who you’ve broken up with twice already? Just because there’s sexual chemistry doesn’t mean you should be in a relationship. Isn’t that self-evident? There are other people to have sex with.

  21. Life is waaaay too short to date guys who only want to be with you at their own convenience.

    LW, move on.

  22. snarkymarc says:

    She lost me as soon as she named him “handsome”. I’m surprised she didn’t name him “Mr. Magical Dick” or “Mr. Fucks-me-so-good”. If this is a real letter the LW really needs to grow up.

  23. He likes having sex with you, but it sounds like that’s about it. You can’t make someone want more than that, no matter how much you want it. and trying is just a waste of time. The fact that he’s had the opportunity to have more and hasn’t taken it is all you need to know anyway. This guy may be super great, but the No. 1 criteria on your list, before being handsome or smart or funny or whatever, should be that he’s interested in you. Too many people put that way too low on the list or don’t include it at all.

    This is an assumption, but you seem like the type who is going to romanticize this and talk about how you just CAN’T let go and go on about him completing you and whatever. But this isn’t about some kind of piece of literature where harboring secret feelings is mysterious and dramatic. In real life, you simply make choices. And the choice here is whether to fawn over a guy who just likes having sex, and you happen to be open for business, or to find someone you like who also likes you. I’d choose the latter.

  24. Laura Hope says:

    Believe it or not, you can have real passion and great sex with a solid, stable, trustworthy guy.

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