Asked by Terri on
How do I get my bestfriend to fall in love with me?
I have been dating my best friend for the past 3 months. We have been very close for five years and share a lot in common. I know a lot about his past including about his five year relationship that ended when he found out that she cheated on him. Due to this in the 2 or 3 years since then he has had trouble making a relationship work, most of them ending before 3 months. He once suggested that he is usually purposely choosing girls that are not right for him. In these relationships he generally would not get attached to them. He would even reschedule his plans with the girl if he's friends had something else going on, tell them they couldn’t stay over because he had things to do in the morning or even give them cab money at 6am so they would go home before sunrise.
He would break it off with them for many reasons... one girl was baby crazy, another was too high maintenance, and another tried to move in and did some other crazy stuff. In our friendship he would open up more to me than he would these girls... about what was wrong and his worries about how "screwed up" he was.
However, one night we were drinking and we slept together. We decided that we were just going to leave it at that because his relationship issues would probably lead to a rocky relationship and the end of our friendship. But this incident seemed to make us closer as friends. We saw each other more often, would joke about the whole thing, and would even have sleepovers where we just cuddled and chatted. I having intimacy issues of my own was okay with that though neither of us was seeing anyone else.
Finally, one night we started making out soberly but decided to postpone having sex. However, three days later we slept together and then started dating. We took turns coming up with these creative dates for us to go on, we would hang out with my cousins, he would call me and text me randomly with little inside jokes. On new years (about 2 weeks into our dating) we were both going downtown with some friends and planned to meet up for a new years kiss. However, he forgot his phone! I went home to my parents house unhappy because I hadn’t heard from him. However, I got a call from him at 3am when he got to his phone and he proceeded to walk across town in the middle of winter at 3am to my parents house just to give me my new years kiss. I was surprised because I wasn’t seeing any of the things he told me he did with other girls. He was the most thoughtful and considerate boyfriend I have ever had. It was effortless and easy. He seemed to be getting closer and closer to me as time went by. Inviting me over for weeknight sleep over’s and suggesting coffee with my family. One night when I said I had to go home for the night, he begged me to stay and ended up falling asleep in my arms on the couch.
Then it was valentines day. We planned a low key night because I am a little uncomfortable with romance and usually never participate in Vday. However, my ex boyfriend who I have kept a good friendship with was coming into town that day for a couple days and didn’t know anyone else in town. I was upfront with my guy about it and assured it would not interfere with our night! Our valentines day was awesome. He took me to a beach he took me to a year before when I had come home for a couple or days from Dublin (I was living there at the time). He had admitted to me previously that that on that particular night, a year ago, he had wanted to kiss me but chickened out because he didn’t know how I would react and wouldn’t be able to anything about either outcome because I was leaving the following day. So for valentine’s day he took me there so I could get the kiss I was “supposed” to get the year before. Everything seemed right and was progressing well. We were happy, had fun together, and we were both getting over bits of our relationship hang-ups. He even attended a seminar for a group I volunteered with in support of me. Then he had to leave for a trip to visit some friends and family for a week. (It just happened to be the same day my ex was leaving to go home). I had been in support of the trip and I have always trusted him. The week went by and I started to miss him, but I wouldn’t ever say that too him least he interpret that as ‘attachment’ (which scares him) and make him run away. He had asked me to pick him up at the airport and it was a moment out of the movies almost. On the way home he shyly but genuinely admitted that he had missed me and that he “never misses girls”. I then reciprocated! We spent about an hour going over his picture’s but he was tired from the trip and had to work in the morning. Over the next week we saw each other 2 or 3 times but we were both super busy and couldn’t really spend more than a couple of hours.
Finally we were going to have a date night the following Friday. I went down to his house and I could tell there was something up. He said that he wasn’t sure about us and was grappling all day long whether or not to say something. He said that he felt like we were friends. That his feelings for me, while they increased in the beginning had plateaued. He said that I was everything he wanted in a girl and had so much fun with me and cared for me… but his feelings had plateaued and while he should be in love with me by now, he wasn’t. He said he was so screwed up that he can’t fall in love with the girl that had everything. He said he needs me in his life and hoped we could still be the friends we had been for 5 years.
Then he proceeded to vomit for the next 8 hours. I stayed until the next morning, rubbing his back while his head was in the toilet and getting him water. He said he appreciated it and was really glad I had stayed. I got up early the next morning and decided I had to go. I woke him up to see if he needed anything and said goodbye. He said he was still sick and would go to his parents house until he was better. I got a text message from him later that day thanking me again but I did not respond. He stayed at his parents house the next 4 days and only went back to work today.
I haven’t spoken to him since because I want to give him his space. But I do really want to be back together with him. I think that possibly the combination of my ex being here and him getting too close to me for his comfort left him feeling vulnerable so he split. Are my assumptions possibly correct? Did he break up with me because he was scared or because he could never possibly love me? What do I do now to get him back?
Thank you!
Signed, missing a best friend and even more so an amazing boyfriend.

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I completely agree with adrian. I think you just need to be patient like you are doing, give him his space and I believe he will contact you on his own.
This guy seems to withdraw when things get to personal and he knows that about himself and so do you. This is just another part in that cycle, he is looking for an excuse to find a problem so he can withdraw. Give him space and hopefully he comes back around.
Honestly, I don't think your ex has anything to do with anything that's going on. It didn't sound like he found it to be an issue and neither did you. It sounds like this guy himself has commitment/self-esteem issues. He doesn't want to be in a good or serious relationship because he feels vulnerable and doesn't trust in love. He probably has such low self-esteem that he doesn't believe anyone could ever love him or that he deserves to be happy with someone. If you want to pursue a relationship you're going to have to be very patient with him until he gets over whatever problem it is he has. I imagine it's going to be a back and forth roller coaster with him where he's going to try to dump you every month saying something like, 'he doesn't deserve you' or 'he's so messed up he can't have relationships' and then keep getting back with you. Clearly you two are dating and he is into you. Maybe you can help him get over all his weird issues just by being patient and just being there for him. But recognize that it's going to take its toll on you too. For now, just give him his space like you are doing. Let him contact you and apologize for his behavior on his own.