Should I Get Back Together With My First Serious Boyfriend? Ask A Pro

By The Head Pro


I have only been in love once in my life. While I think it is possible to love multiple times in a lifetime, I also think it's equally possible to never have as strong of a connection as you did with one person. I think everyone has that person, whether they end up together or not. I met this person when I was fifteen and we hooked up for two years before entering a relationship. We were in a relationship for five months before moving in together. We lived together for three years and broke up last August. I was so young when I fell in love with him that I didn't really know how to be in such a serious relationship, especially since we moved so quickly. We were both at fault for the breakup, but I would say more of it was due to my own immaturity. But I feel that this past year, in combination with the experience of losing him has made me grow so much.

I saw him yesterday for the first time in a year. He got into a relationship a month or two after we broke up, but they just broke up because she took a job across the country. When we broke up, we each took a dog and we met up at his place because he has a dog park. We spent like ten straight hours together and just hung out like nothing had changed. He didn't mention anything about our break up, but did say that his most recent relationship was almost more unhealthy than ours. Because instead of fighting things out like we did, they pushed it under the rug and never talked about anything. We had sex. It just happened. And it was amazing, because obviously after you spend so long with someone, you just know what they like. Then he cooked me dinner and we didn't talk about it. He walked me out and texted me that it was good seeing me and our dog Bilbo. I guess my question is how do I approach trying again with him? It was so good to see him and be so comfortable with him and I don't want to push too hard or make him uncomfortable. But I can't not try when I still have so much love for him and we still get along so well together. Any and all advice much appreciated.



Dear No, it’s Not Unrequited,

Ok. People (maybe you?) will bitch about how I’m not actually answering your question, but: You do not need to get back with your ex, and not just because he himself described your relationship as “unhealthy,” even more so than the one he recently exited on his own volition. Your beliefs on love are a little misguided. I think you’re confusing “connection” with “intensity,” in which case, sure, maybe there will be one person for whom you’ll have intense feelings, unmatched by any subsequent relationship. I have bad news, though - it has nothing to do with that person, and everything to do with the fact that you began dating them at 15. Hormones, novelty and all sorts of “first experiences” convene to make that kind of love unique to your teenage years, which is a good thing. That kind of love is fucking exhausting.

Connection is about breadth, not just the depth of intensity. It’s not the stomach butterflies - it’s all the little, altogether more mundane shit that no one writes songs about. It’s someone who, after tallying up a list of abstract and indescribable “must haves,” makes you altogether happier than you’d be without them, and almost never hurts, betrays or disappoints you. So while it’s silly to believe the universe somehow conspires so that you only get one shot at that, there’s some truth to it in that it’s very rare to come across people that manage to check off all the boxes on your imaginary list. That’s why most people, even the most prolific casual daters, don’t end up having THAT many relationships in their lifetimes.

Even if it were true, you’re what, 18 years old, or so? I strongly doubt that your One True Love is the guy for whom you fell madly in love before you could legally drive. Going back to that intense love is like an alcoholic falling off the wagon - a brief euphoria immediately followed by equally strong sadness and regret. Of course you relished your time together - familiarity is incredibly comforting - but it’s not an indicator that you should get back together. I promise you, at some point you’ll get involved with someone you love in an infinitely more fulfilling way, and you’ll look back and wonder what all this teenage bullshit was even about.

Requited Kisses,

Head Pro

Dear head pro,

I need your help. Badly! Im a dude btw. So i went to the wiz concert last night at jones beach and this really hot girl sat next to me with her friend. Ive been trying to find her on facebook and instagram but i dont remember her name or have her number. She was eyeing me down the whole night and i need to just find out who she is. Im emailing you because i no she reads betcheslovethis and it is the only way i can get in touch with this babe. It would be great if you can help me find her. Here are some details: she was a brunette and was with her redhead friend with a nose piercing. We sat in the lower level (orchastra F row PP). If u were looking at the stage we were to the left but in the middle. She was in her early 20s. I think that narrows it down a lot and i hope you can help. Thanks


Dude, this is not fucking Craigslist, but fine: If you are a “hot” “girl” who attended the Wiz concert at Jones Beach this weekend, Perry is looking for you. He was sitting in the lower level (orchestra F row PP, specifically), and you were “eyeing him down the whole night.” You were somehow both on the left and in the middle. Email me, and I can then get the two of you in touch.

Dear Head Pro,

I broke up with my boyfriend a few weeks ago and have been heartbroken ever since. I broke up with him because I never really saw myself ending up with him but now that it is over, I am so much more upset than I ever imagined I would be, so now i am reevaluating my feelings on us breaking up. Last week I swallowed my pride and reached out to him and asked if we could look at getting back together and maybe work through things and possibly try again but he said he is over us and is even looking to go out with other girls now. It is really hard to accept that he is over us in less than three weeks after being together for nearly two years. Of course I was shattered and considering I went back to him, I don't think it is a pride issue. I know everyone processes break ups differently, I just want to know whether you think he just feels that way now but will change his mind in the future or if you think it really is over for good. I know I should just let go and work on getting over him but I feel like we may not really be over. Am I delusional or is there a shot?


Not so green on the other side.

Dear Not so Green,

Um, what part of “I asked him to get back together and he said ‘no’” leads you to wonder if there’s still a shot? You’re basically saying “he expressed no interest in this but I don’t value his thoughts or feelings in the matter, so I’m looking for a different angle.” Do you not think that he’s aware of your general disregard for his feelings, or the fact that you broke up with him because you found him unworthy? Those are things that tend to leave a bad taste in people’s mouths. Why is it so hard to believe he’s “really over you in three weeks after being together two years?” You apparently felt the same way, hence the decision to end the relationship.

Also: It is not that serious. You have been broken up for less than a month. That is hardly enough time for either of you to process the breakup, let alone have a serious conversation about reconciliation. It could indeed be a pride issue (not sure why you think it’s not), since after having his pride hurt by being dumped he now has it back by holding out on you. That, or he could just be genuinely over it. Too soon to tell. You all need to not speak to each other for two months, and then talk about it at that time. Nothing good comes out of decisions made in the heat of the breakup aftermath.

Green Kisses,

Head Pro




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