Could we be more than Friends?

[PinkDotsXOXO]

Hey all,

I don’t want to be perceived as a home wrecker but here it goes. I’ve been friends with one of my guy friends for 9 years. We dated when we were 16 for about a month and then broke it off (due to mostly immaturity among other reasons). However since then, I’ve gone through periods of time where I’ve liked him but either I was dating someone or it wasn’t a good time for us to give it another try. He later started dating this girl and they stayed together for quite some time until they broke up. In the not so recent past they have now gotten back together. When him and I hangout its usually just the two of us. So a few months ago, after a few drinks, I got brave and told him how I felt about him and he said we’d talk about this when I wasn’t drunk. Nothing really happened that night except a longer hug then I usually give him and us falling asleep on my couch close together sorta cuddlingish. I didn’t wanna make him choose so I started dating someone else and we broke up. (For reasons unrelated to him) Fast forward to now: A few weeks ago he moved to another state 2.5 hours away to be with his girlfriend. Lately, she hasn’t been home because they’ve been fighting and shes been sick so she will go stay with her parents. We’ve started talking more since he moved away. He’s been alone at their house a lot. On more than one occasion I’ve made it clearly obvious that I’m flirting with him. Tonight I told him I’ve thought about kissing him in the past and asked him if I was making him uncomfortable to which he said no hes fine and he guessed I felt that way. Our conversation turned sexual which in the 9 years ive known him we’ve NEVER talked like this with each other before. I don’t know if he was joking but we talked about possibly fooling around & drinking when he comes back here and we actually started planning it and talking about what we wanted to do together. Were such good friends and ive known him for such a long time and were comfortable with each other. I actually like him but I feel horrible because he’s been with his girlfriend a while but I don’t know if he’s truly happy with her. I don’t know her well at all in fact I’m not a fan of her because back in the day she asked if I would mind if my then boyfriend would go to prom with her friend. Plus she broke his heart a while ago. He really is a great guy, has helped me with a lot of things and we’ve remained close. Is this a safe thing to pursue or should I not rock the boat? Thanks in advance for your advice!

[SleeplessIn]

As long and as well as you indicate you have known him, it seems to me that you could simply ask him if he is happy with his girlfriend. It's the kind of question that a friend should be able to ask, his reply should be enlightening. Depending on how that conversation goes, you might be able to mention that if things don't work out with that girlfriend, you'd enjoy seeing him on a dating basis in the future.

 

This lets him know you are interested, but it also allows you to simply be supportive of him if he is hoping that things DO work out with his girlfriend.