Dear Wendy
Dear Wendy

“If I Keep Sleeping With Him, Will He Eventually Want Me Back?”

My ex and I were together for a little over a year — an intense, beautiful year. We were both extremely happy and in love. I had never felt anything like this before, and I felt like I already had a bond with him when I first met him. He broke up with me three months ago because he doesn’t think I’m the one. It puzzles me how he thinks we don’t have a future when our past and present are so beautiful. It has been hard for both of us to walk away because we both love each other, but he feels he’s saving me from a dead-end relationship and he wanted to do right by me.

During these past three months we have talked back, and forth and recently we slept together. We’re still not back together, but I’m wondering, with time and distance and/or sleeping together, if men eventually regret breaking up with you? Is there any possibility a man has some sort of epiphany and changes his mind about your being the one or not? — Puzzled

Sure, men and women both change their minds about breakups, but it doesn’t typically happen in the form of an epiphany after sleeping with an ex. In fact, I’d say in your case the opposite is likely to happen: As long as your ex-boyfriend still gets the benefits of your company, companionship, friendship, and sex, he has literally zero incentive of getting back in a relationship with you. And here’s the cold hard truth that you really need to hear: Your relationship wasn’t that “beautiful.” It wasn’t that great or your boyfriend wouldn’t have ended it. I believe YOU thought it was wonderful and intense and amazing and super special, but he didn’t. Or, if he did, he stopped feeling that way. My guess is he felt you were way more into it than he was and so then, because he didn’t want to lead you on by staying in the relationship, he ended it. Does that mean he stopped caring for you and enjoying your company and having sex with you? Obviously not, which is why he’s still into enjoying those things. He just doesn’t want strings attached. If that ever changes — and it probably won’t — it’s not going to happen by your continuing to hang out and sleep with him. You need to accept that the relationship is over and MOA.

When I was in high school, I had a crush on a boy. Fast forward to four years later, and he’s still on my mind at least once a week — sometimes for an entire day straight thinking of nothing but him. We were friends, we never dated, and I swear this must be what it’s like to have an ex-boyfriend. I have tried everything I can think of in attempts to forget about him. I’m aware that he’s not a good fit for me, that he’s been rude in the past, and that he’s not even in the same province as I am anymore, but still I can’t help but think about him A LOT. I tried convincing myself to hate him, but it doesn’t seem possible. I don’t even see him anymore, don’t have him on any social media… I don’t know what else I can do to cut him out of my life.

Do you think this will last forever? I have had interest in other guys since meeting him, but none of them have lasted very long at all. — Still Crushed

This actually is NOT what it’s like to have an ex-boyfriend. I have ex-boyfriends and never did I spend entire days thinking of nothing but them, save for maybe my first ex-boyfriend and only in the weeks after our breakup (certainly not years afterward!). What you’re describing is an unhealthy obsession that has morphed from what was probably a harmless crush to something that is distracting you from real life. I don’t know what is actually going on in your real life that you feel you need distracting from — either consciously or subconsciously — but there must be something.

The obsession is nothing more than a symptom and it’s your job to get to the root cause and work on fixing it. The root cause is not a crush on this guy you barely knew, never dated, and don’t seem to even really think fondly of. The root cause could be, but is not limited to: loneliness; anxiety about your future; anxiety about your present; fear of being alone; fear of being in a relationship; fear of being rejected by someone in your real life whom you might pursue; family problems; general depression.

To figure out the root cause and to start addressing it, start by being honest with yourself about what you might be avoiding, especially at the times when you fill your days thinking about this dude from your past. What is something that begins to give you anxiety when it crosses your mind? THAT is probably the root cause, or one of the root causes. If you need help identifying that thing, talk to someone you’re close with and trust. Ask her or him to be honest with you about what it is they think you’ve been actively avoiding. And then stop avoiding that thing. Talk to a counselor if you need help, or consult a life coach or career counselor.

There is nothing you can or need to do to “cut that guy out of your life.” He’s not in your life. It doesn’t sound like he ever was. You aren’t even obsessing over him anymore but are obsessing over the idea of him. You are filling your mind with the idea of this person because, as long as your mind is filled with him, you don’t have to fill it with whatever it is that’s fighting for your attention. You can’t fight it forever, and the sooner you deal with it and move on, the sooner you can begin to heal and eventually be in a place to have a real relationship with someone who is more than just an idea.


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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.

18 comments… add one
  • JD March 23, 2018, 9:25 am

    I don’t agree complete with Wendy that you just stop thinking about an ex. I have an ex I will always think of and it has been many years. That being said it was a very long relationship, he is in fact my ex not just a crush and it in no way impacts my life. It is more of a “I miss that person because he was a great person and it sucks it ended” kind of thought. Usually it just is something that reminds me of him. You have built something that was actually nothing into a bit of an obsession. That is not healthy. Even if you had been together it wouldn’t be healthy.

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  • Fyodor March 23, 2018, 9:26 am

    “My ex and I were together for a little over a year — an intense, beautiful year. We were both extremely happy and in love. I had never felt anything like this before and I felt like I already had a bond with him when I first met him. He broke up with me three months ago because he doesn’t think I’m the one.It puzzles me how he thinks we don’t have a future when our past and present is so beautiful.”

    I think that you need to engage with the fact that while it may have been beautiful for you it was not for him and that is why he broke up with you. It’s always creepy AF to me when people declare that a relationship was “perfect” for the other partner. It reflects a fundamental inability to see the other person as someone with their own wants and needs. Your subjective experience is the only one that counts, right? He’s just a participant in that.

    Also, your false belief that he has committed some sort of massive cognitive error is causing you to keep wasting time on someone who broke up with you. Surely he will realize what a mistake he made and come back! But he didn’t make a mistake and isn’t coming back.

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    • JD March 23, 2018, 9:50 am

      Right! If someone says they don’t want to be with you, believe them. Also, why would you want to be with someone who doesn’t want to be with you? My guess is she will keep doing the same, believe they are back to madly in love and be writing again that she is so hurt because he still doesn’t want to be with her.

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    • mybluedolly March 24, 2018, 3:20 pm

      Totally. If you date a guy who says he’s into you, but doesn’t ACT like he’s into you: He’s not into you. If you date a guy who says he’s NOT into you, but acts like he is: He’s not into you. You gotta have both mouth and action to have something, otherwise what you have is a whole lotta nothing.

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  • Rebecca March 23, 2018, 10:16 am

    De-lurking for the first time in a while to say, LW1, Oh, honey…

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  • Lianne March 23, 2018, 10:47 am

    LW1 – No. He will keep sleeping with you but it will not change his mind. I did this with my ex for 3 years. THREE YEARS I waited for him to change his mind. He didn’t and started dating someone new, whom he married. Now, I am several years removed from that situation. I am also married with one kid and another on the way. Time and distance bring clarity. He was telling me maybe we would end up together, but now I know he was keeping me on the line because the sex was good. And it was. I wish I had recognized it for just being that and not wanting more…it would have made it so much more enjoyable, if I’d had the perspective I do now. But I didn’t. And you don’t. So, MOA. That’s it.

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    • csp March 23, 2018, 11:09 am

      LW1 – Can I add to this. Don’t be the “Cool Girl” who is “really chill” with a crap situation. This is a very universal story and so many guys are willing to take advantage of a woman who will settle to be a hook up and then praise her for being a “Cool Girl who doesn’t get emotional about stuff”. (maybe I am talking about my past self too much here)

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      • JD March 23, 2018, 11:15 am

        I’ve never understood the “be the cool” girl thing. Don’t be an overbearing bitch but be you! Otherwise you are just setting yourself up for misery. You’ll pretend to be “cool” with whatever until you aren’t even yourself anymore and the person you are with is dating a lie of who you are. Recipe for disaster.

      • Lianne March 23, 2018, 11:33 am

        YES. I was always trying to be the cool girl. God, I wish I could shake myself sometimes haha.

      • MissD March 23, 2018, 11:34 am

        I think we all went through that. I definitely did in my early 20s.

      • Ruby Tuesday March 23, 2018, 11:57 am


  • csp March 23, 2018, 10:47 am

    LW2: I think it is normal to think about “What might have been” or “The one that got away”. I do think that Wendy is right that usually when these thoughts creep in, it is when you aren’t thrilled about your current situation or prospects. I think it is worse now when you can see people on social media and we spend less time IRL.

    My suggestion is to get busy. go on a screen free cleanse. Start filling your time with friends and new activities. The phrase “Idle hands are the devil’s playground.” is so true because I feel like unhealthy thoughts creep in when we are bored.

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  • Lisa March 23, 2018, 6:15 pm

    LW1 he dumped you and now he’s just getting some free easy booty from you while he plays the field and looks for Ms. Right which he clearly does not think you are. Don’t allow this you are asking to be hurt. Sex does not equal love for men it equals sex that’s all. Will he realize he made a bad decision and want to get back with you? Unlikely but if he does it’s not going to be while you are giving it up for free. The best thing you can do is cut off all contact and pretend he no longer exists. If he wants you he will make an effort you don’t have to force it and the only way I would take him back is with a ring or other serious commitment. And you are missing out on Mr. right for you wasting your time on this dude.

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  • dinoceros March 24, 2018, 5:30 pm

    LW1: Sleeping with someone after a breakup doesn’t typically make that person want a relationship. If they wanted a relationship, then they’d still be with you. But most likely, they want sex but not a relationship. If you don’t want sex without a relationship, then stop sleeping with him.

    LW2: Yeah, this isn’t what it’s like to have an ex boyfriend. You don’t pine over them four years after the breakup. You say you thought only about him for an entire day. You may want to see a counselor. Obsessive thoughts that impede your daily functioning aren’t normal, even if it’s over a crush.

    You may not see him in person, but you “see” him whenever you allow yourself to sit around and think about him all day. Thoughts aren’t something that just happen to you. Sure, you can’t fully control them, but you can decide whether when he pops into your head, you sit there and think about him or whether you get up and do something else, or choose to think about something else. (Like, “Hmm. Let me think about my shopping list.” “Let me go watch a movie.”) You can’t get over someone if you carve time out of every week to just think about them for hours on end.

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  • Dear Wendy March 25, 2018, 11:44 am

    From LW2:

    “Thanks for replying so fast! I read your reply, and of the options you gave for root causes, I could see multiple that apply to me.
    For loneliness, you mentioning that made me realize it might just be the friendships I had in high school I’m missing. There, I had people to hang out with every day. Since then, I made only 1 good friend in college whom I rarely shared class with, and then got kicked from my year, so I’m back to being alone. I guess I didn’t realize how it was affecting me.
    I also have a LOT of anxiety about my future, which I’m actually seeing a doctor for this week to see if it’s something I should be concerned about. Nursing school is insanely hard and brings up anxiety issues you might never have to deal with if I’d chosen another career.
    Lastly the general depression idea, I don’t know if it’s right, but it’s something I’ll look into, because I feel like it might be a possibility.
    Probably I’m thinking about him to avoid thinking about school, the fact I failed a course and now am extremely worried I’m not smart enough to be a nurse, my lack of friends at school, and just overall being worried I’m never going to be good at anything but working at a dry cleaner (I may be slightly spiraling)
    I’ll take your advice to talk to some sort of counselor, and one of the comments mentioned that if I make myself more busy with new hobbies I might be able to concentrate on something good for a change, so we will see how I go!
    Thanks again :)”

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  • Dear Wendy November 13, 2018, 6:23 am

    From LW2:

    “Heyo, I can give an update but idk if you’ll like it.

    I still think about him fairly often, but I’d say I’m less obsessed at this point, maybe once a week he pops into my head. The problem is, I still super miss him a lot of the time. Now and then he comes to town and I rush to find time he’s available to hang out. At this point I’m aware nothing will ever happen between us, but it makes me so happy to see him I don’t see the point in shunning him. Any time we talk I start the conversation, but he will keep up a messaging session if I start one. My question at this point would be, is what I’m doing not smart? I tried to address the issues I might be trying to ignore since your last reply, but then I found one of my close friends who also hung out with him is feeling similar, we both miss him a lot of the time. Is what I’m doing normal, or unhealthy?”

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    • Dear Wendy November 13, 2018, 6:23 am

      If missing him and thinking about him and then rushing to see him when he is in town is occupying your mind and focus enough that you don’t think about or foster other potential relationships, then it’s a problem. If you still hold out an inline of hope something might develop between you, it’s a problem. If his not liking you back the way you wish he would or his not initiating conversations with you makes you feel bad about yourself, it’s a problem. And what I would advise is completely cutting him out of your life – stop texting him, stop seeing him when he’s in town – so that you can truly move on and be emotionally available, as well as physically available, for someone who can reciprocate your feelings.

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    • LisforLeslie November 13, 2018, 7:00 am

      Sounds to me like this person has the gift of total charm. There are people who have this magical quality and you want to be in their orbit. But they can only give you a tiny piece of what you are really looking for, because they give their charm to as many people as possible.

      I agree with Wendy. You need to treat this with total cut off.

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