Should I re-ask my shy best friend 5 years later?

[CathC]

Long Post... sorry bout that...

 

My best friend is a pretty awesome guy. We are very different from eachother and he is a rather shy man who comes from a conservative family that is a different religion from mine. I can't see myself ever wanting to belong to the church he belongs to.

 

Despite our differences... I absolutely can't get enough of him. A long time ago (over 5 years during undergrad) I told him I liked him. I had known him at that point for about 6 mo. and he told me he didn't see me that way at that time. We remained 'friends'.

 

Well, time passed. We are at grad school together now (both in mid 20's) and part of the reason he chose this college was because I'm here. We see each other about 4 days a week and we call/email/come over to one another's homes equally.

 

He talks about relationships/marriage/kids/husband wife stuff to me often so I know he isn't gay, but he hasn't dated anyone since I've known him. I have met all his family, he invited me to his dad's wedding, and I truly believe his mom thinks we are dating since she lumps his brother's girlfriend and myself in the same category.When we go out to get tea or go to a show he will offer to pay maybe 50% of the time.

 

BUT... I invited him recently to come on a mini-vacation with me and my family and he didn't seem to be interested. We often hug and have all of that eye contact awkwardness, but I sometimes wonder if I am just imagining it. When other guys talk to me he comes and will stand right next to me or put his hand on my shoulder (not in a romantic type way though). BUT... when it is just the two of us and I try to do something physical-ish, he doesn't seem to respond all the time... only some of the time.

 

As you can probably tell. I am CONFUSED!!!

 

He is so shy, but has been coming out of his shell lately. I can't shake my best friend. I really want to date him, but I don't want to ask for fear that what happened 5 years ago will happen again.

 

Does he like me? Are these some major mixed signals? Should I keep waiting? Is this one of those situations where I should risk the awkwardness? I would love some advice!!!

[CathC]

Thanks Sunshine,

 

It is just so tough to figure this one out. What are some ways that I could ask that would be non-threating?

[Gray Fox]

go for it