Wait, isn't this the plot of When Harry Met Sally? OP, you should:

A. Watch that movie
B. Go for it

Yeah, have a drink or two and then tell him you have a confession. Mention the previous encounter and how things got awkward because you we're caught off guard but that now that you have gotten to know each other so well, you think the romantic thing might be worth a go if he was still interested.

This will go nowhere. You view him as weak for not having the courage to pursue you even if he isn't and will always believed you settled. At best you will always be looking for the greener grass.

I don't know how relevant this is but for three years I was good friends with a guy I worked with. We were both young MBA's working long hours along with others and having a real social life was tough. We flirted a bit...or at least I did.... but as co-workers it didn't go anywhere. I finally decided to see if there was anything there and one day I seriously flirted with him which sort of confused him but he went for it. We had one date and after that we were together all the time. That was over 30 years ago and we are still going strong. I know you are looking for a male POV but I know my husband loved that I took the lead.

I would tell him the truth. You weren't available that way when you met, but now you are wondering if he'd like to try something more.

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:He made a move that you shut down. If you want to test the waters you'll have to make the move this time.

+1

It's on you to change the status quo, OP.

OP here: Yeah, I do get that might be the big issue. I just don't want to do it and then get the, "You're a sweet woman, and I really like you, but not that way..." speech and make him feel like he can't be close to me without me getting the wrong idea. I mean, I want HIM in my life, under whatever circumstances make sense, more than I want to f*ck him. (Although, the f*cking sounds good too. I'm pretty sure he would be great in bed.)

Guy here. Because you shut him down before, he is not going to make the next move. #metoo. Particularly if he is a good person.

I would tell him "you are my best friend, I want you in my life in any fashion. With that said, I am interested in finding out if there could be more." Then, lean in for a kiss. If he responds, guide his hand to where you wan them to go. or suggest going to a private spot.

PP here. Let me tell you a story. Back when I was in college, 30+ years ago, I had a crush on this classmate. But I was afraid to lose the friendship. So, we went out as friends but never more. After graduation, I ran into her once or twice at meetings. We chatted, but that was it.

Many years later, her name pops up on "people you may know" on facebook. We started talking a little bit. I found out that she was waiting to ask me out. She finally decided I must be gay or something, as I never dated. Nope. Just shy. It probably would not have worked out long term, as I was not ready for a relationship at 22, but it could have been fun. (Nothing happened later, as I am happily married now).

Invite him for dinner. Drink.some wine. Confess that you gave never felt closer to him and wonder if he feels the same.

Yes he is into you. His feelings haven't changed. But do note this...it's not always as seamless a transition as it might seem (eh, not just adding sex to what you have, everything changes including unspoken expectations). It's tempting nto launch head first but if you can, take it slowly. Try dating him. And report back!

Anonymous wrote:

Anonymous wrote:

Anonymous wrote:He made a move that you shut down. If you want to test the waters you'll have to make the move this time.

+1

It's on you to change the status quo, OP.

OP here: Yeah, I do get that might be the big issue. I just don't want to do it and then get the, "You're a sweet woman, and I really like you, but not that way..." speech and make him feel like he can't be close to me without me getting the wrong idea. I mean, I want HIM in my life, under whatever circumstances make sense, more than I want to f*ck him. (Although, the f*cking sounds good too. I'm pretty sure he would be great in bed.)

Guy here. Because you shut him down before, he is not going to make the next move. #metoo. Particularly if he is a good person.

I would tell him "you are my best friend, I want you in my life in any fashion. With that said, I am interested in finding out if there could be more." Then, lean in for a kiss. If he responds, guide his hand to where you wan them to go. or suggest going to a private spot.

Has he ever brown stamped you? If so, that will be a test of your feelings for each other. If not, the relationship is still likely in a nascent, still-developing state.

Anonymous wrote:

Anonymous wrote:He made a move that you shut down. If you want to test the waters you'll have to make the move this time.

+1

It's on you to change the status quo, OP.

OP here: Yeah, I do get that might be the big issue. I just don't want to do it and then get the, "You're a sweet woman, and I really like you, but not that way..." speech and make him feel like he can't be close to me without me getting the wrong idea. I mean, I want HIM in my life, under whatever circumstances make sense, more than I want to f*ck him. (Although, the f*cking sounds good too. I'm pretty sure he would be great in bed.)

Go for it. Just don't break his heart.

Anonymous wrote:He made a move that you shut down. If you want to test the waters you'll have to make the move this time.

+1

It's on you to change the status quo, OP.

He made a move that you shut down. If you want to test the waters you'll have to make the move this time.

Not a male.

I have never ever regretted making it clear that I want more from a friendship or making a move. It has always been received well.

So, I am a straight woman, and I have this male friend who I have been pretty good friends with for a couple of years now. We got along like gangbusters from the second we met, and initially at least, I KNOW he was interested in it being more than friendship, at least casually, although at the time, I was not in a position to be able to consider that. Lots of flirting on his end--eventually, he made a physical pass that he aborted after realizing that he had startled me, and we've never spoken of it. At no point did he actually use his words to actually communicate what he wanted, what he was feeling, etc.

So, now we've sort of fallen into this deeply emotionally intimate friendship--my guess that is that the only person who might know more about him than I do is his ex-therapist, and he's pretty sensitive to what's going on with me too. There's definitely some mutual affection--I might have thought that maybe I had fallen into more of a little sister role for him since he had stopped actively flirting, but he, for sure, doesn't treat me like that. When we're together, he still treats me like a date--we share food off the same plate, we talk about EVERYTHING (you know, except us, lol), he never wants to let me pay for anything, is quick to share his jacket, etc. The emotional/intellectual chemistry is off the charts, and I think the physical is probably still there, but we've just put up this platonic wall blocking it. I do think it's entirely possible that he's still very interested, but doesn't want to be pushy and also very much values my friendship enough to be cautious.

I am now in a position to maybe think about more with this friendship, and I am not against sucking it up and making a move, but I guess maybe I need someone neutral (especially men!) to give feedback on the situation before I have enough guts to do it.