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Kind of a long story but i’ll try to bullet it.  Basically, I need a neutral party perspective on the situation since my friends tell me what I want to hear.

I’ve known this guy since I was 6 years old.  We were on a recreation swim team together until we were about 12.  We didn’t really hang out since I was more sociable and was there to have fun and swim and he was moreso there to just concentrate on swimming.  He was such a good swimmer/smart kid and would hang out with the older crowd.  My mom would always be like “you’re going to marry him someday, he’s such the perfect little kid.”

Eventually we both had quit and 4 years went by.  My high school started a swim team and I figured why not join.  I was captain and a social butterfly as I had been my whole life.  It just so happened our coach had been one of the best coaches from the recreation team I used to swim with.  Along came the “perfect little kid” as a teenager now.  He was still very smart and very sociable, but moreso with adults.  He didn’t have much experience in dealing with girls and it showed.  He was very attractive so all of the younger girls loved him and would cling to him and I was just friendly.  We would talk every now and then which eventually led to him and I meeting up in my car after practice and chatting/catching up on life.  He would say he wanted to kiss me and would peck me and literally run away.  One night I told him I would show him what a real kiss was and told him to pull over and gave him a “real kiss.”  It was a typical high school situation.  He wound up going to a private college in MD. and I a state school in NY.

Every now and then we’d keep in touch, he wrote me some letters every now and then and had told me he wondered if we could’ve ever turned into anything.  I didn’t think so in my head, since I thought we weren’t really on the same level.  He was more reserved and “nerdy” and I was more outgoing and I guess into the “party scene.”  Time passed, he had gotten into a relationship.  We’d try to hang out on our breaks but never did, and that was that.

Here I was now summer after graduating college in September (2008, this is recent, now we’re more grown up obviously).  I was out with three of my girlfriends at a local bar dancing and turned around and banged into him.  I hadn’t seen him in  5 years and definitely didn’t expect it under that circumstance.  He was with another girl who pulled him away and I had seen him for 10 seconds.  I emailed him later that week and asked him why his gf pulled him away so quick.  He responded that it wasn’t his gf and that we would hang out soon.

3 months later we went out to dinner.  My mom opened the door for him and went nuts over him.  I walked out and got the weirdest butterflies.  We had a great time at dinner even though he told me he was in a “serious relationship of 3 years at this point.”  A few drinks later we were making out in a booth in a wine bar.  (Not so classy).  He broke down at the end of the night saying that he had made a mistake and hated that he had been so shy and msised out on me etc.  (Not talk from just drinking because we hadn’t had that much).  He said it to me multiple other nights online and phone.  We hung out about 8 more times consecutively after that and I started to really care about him.  I was very hesitant though because I knew he had a gf in Maryland.  He would ask me if I had hope that they’d break up for me I said no.  I am a very strong person and do not get very emotional when it comes to expressing myself so I didn’t really.

He started to get shady and “very busy.”  He then online told me he was breaking up with his gf…. for another girl he had went to high school with.  I told him that he was the most selfish person ever and to not speak to me anymore.  2 weeks later we started talking bc I missed my “close friend” which he had become since we had spoke everyday.  They started dating.  Time went by and we began talking again daily but not hanging out.

Finally one night he came over and vented to me about her and life.  I did to him about a guy I was dating.  We didn’t even come close to kissing, nothing.  I was happy.  NOW though we just started hanging out again.  3 timse in the past month (still talking everyday though) and the same thing is happening.  Kissing and cuddling and dinners and movies.  The other night I was going to say we had to end it but it was a mutal discussion.  He said he can’t figure out why he always comes back to me but that he loves his new gf.  I told him that I know he’s not good for me but lose common sense with him.  I know it’s not just lust because I want to be with him even if we’re not hooking up.  But It’s hard to picture us together because we’re at different points in life.  H’es in school still and I have a career.  I think I love him though  and I don’t know what to do about this. 

What do you think he feels?  Why does he keep cheating on his gf’s with me?  What should I do?

Lisa’s Relationship Advice:

Wow, what a story!  It’s interesting after all these years you two seem to keep some kind of connection even though you never really pursued a relationship.  But you still clearly both have some kind of feelings for each other.

This might simply be a matter of the “what ifs” fueling your interest – or there might be something deeper.  But it is concerning that he keeps breaking promises to other women in his life when he cheats with you.  Not a great sign.  However, it’s likely he’s also very confused.

There’s no way for me to know what he’s thinking.  Both of you are drawn to each other though you’re both different in who you are – and where you are in your lives.  I think the question for you is if all this back and forth confusing behavior still works for you.  I imagine there’s some point when you’ll want to draw a line in the sand.  What that line looks like for you, I don’t know.  It could be a total cut off or a promise to yourself that you won’t allow yourself to get drawn into this thing again – but are able to remain friends.

I imagine you’d like to find a committed life partner at some point.  Could this guy be an obstacle to this?  Does he have the potential to be that partner and be the relationship you really want?  Or is he able to break his own cycle (that is potentially hurtful to others and you)? 

Good luck!  Trust your instincts.  At the very least, talk to him and tell him how you feel about all of this. 

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Lisa Brookes Kift is a couples therapist and author or The Premarital Counseling Workbook for Couples and The Marriage Refresher Course Workbook for Couples. 

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