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Grab bull by the horns or let sleeping dogs lie?
#1
Good evening ladles and jelly spoons,

Please bear with me through this as I'm a man who likes a good narrative.

I have a friend for whom I have unresolved romantic feelings and I have the suspicion the feeling may be mutual, although there is a chance this is wishful thinking. We met a couple of years ago through a mutual friend and we've become good friends ever since. There was a drunken night about a year ago when he made a sexual pass at me but I turned him down as he was white girl wasted. I suggested to him in the morning that we try dating but he turned me down saying he didn't want to risk losing a friendship should it not work out and that the timing was wrong (whatever that means?)

To add some context I'm a 32 year old professional and he's a 22 year old student (he finishes his studies this year). I'm 32 but I look a lot younger, people always presume I'm in my early twenties and the younger out of the two of us. I get a fair bit of attention but I believe I have a particular type of attractiveness. I'm tall, slim and 'twinky', a little feminine and fey looking, I guess. He on the other hand is tall and broad, masculine and classically handsome, the type of guy that people check out in the street. I'm reserved, logical, emotionally intelligent but can come across as aloof and cold. He's outgoing and excitable but easily distracted, a little self absorbed and quite insecure at times.

Now since that evening I've kept my feelings to myself but there are moments when I feel that he may have mutual feelings. Allow me to present a couple of anecdotes to illustrate my point...

He asked me if we could go away together so we spent a long weekend in Amsterdam. Nothing happened sexually (he discovered he had an STI shortly after we arrived) but there was a moment when we were in the gay village and he was chatting to some guy that was obviously interested in him. I have friends who live in the city and was chatting to them. This guy who was into him had to leave to meet his friends and my friend suggested we go meet up with him later, I got frustrated and told him "You know, sometimes you're completely oblivious". I immediately regretted it, I knew it was an unfair comment. He didn't get upset though as I expected he might, he just apologised and told me it's fine, he wanted to spend the evening with me anyway and then gave me a look like he was expecting me to say something more. I chickened out though as I didn't want to make the rest of our time away awkward if I was wrong.

On the evening before we flew back we had dinner and as we walked passed the canals on the way back to the hotel he made a comment that I should take him on a romantic canal boat ride. I jokingly asked if he was flirting with me and he said "Yeah, you're my sugar daddy." I just laughed it off and chastised him telling him I wasn't old enough to be a sugar daddy.

A couple of months later we had an argument and fell out. He made arrangements for a house warming party and rearranged the dates twice at short notice. I'm self employed and turned down work on both occasions to attend his house warming so made a light hearted comment making fun of his disorganisation on his group invite. He accused me of humiliating him and I explained that he had lost me a significant amount of money through his disorganisation and instead of getting mad I made a light hearted comment and that he should lighten up. He sulked for a few days and then told me he forgave me which angered me as I felt he was the one in the wrong and should apologise. I decided to take a break from him and didn't contact him for a while. He later rang and apologised and told me that he missed me and that it felt weird not having me in his life.

I told him recently that I was considering a move to Canada and that I was going to spend a month travelling the country to see which city suited me. He got upset and told me he didn't want me to leave. I suggested that he move with me and he agreed but seemed non-committal. He later asked if I could put off my plans until after he had finished his studies so he could come with me when I went to visit and I told him that was fine, just presuming he wanted a vacation. Last time I saw him he told me that he had been researching jobs in Canada and Toronto was the only city that was really offering work in his field. So I was surprised he seems to be genuinely considering it.

He has had a few brief relationships and gets drunk and sleeps about a fair bit. I'm the opposite in that I'm a fairly lucid drunk and don't really date guys as I like my own space and free time but there was a moment last year when I decided to try dating a guy that we both knew who was being fairly persistent with me. When I told him that I was dating this guy he seemed to get a little stand-offish.

Now I'm not sure if there is something there or if I'm just deluding myself. I'm not the type of guy that makes the first move, I wouldn't even know how but I really like this guy and would be willing to make an idiot out of myself if I was more certain that he was feeling the same way.

Part of me feels that he might be interested but another part of me is suspicious that he just enjoys the money. He's broke as he's a student and I almost always pay for the things we do, which I don't mind but I do have it in the back of my head that he might be enjoying the money more than he enjoys my company? Although that might just be my own insecurities talking.

What do you guys think I should do? Grab the bull by the horns and ask him to clarify if there is more going on or just let sleeping dogs lie to avoid ruining a friendship.
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#2
Sounds immature. As far as he using you, I mean probably, not very many angels these days. Just don't think everyone is after your money. There are good people out there. My thing is trust your instinct. Even if this guy isn't using you he's very immature and you are probably a bit of a sucker yourself. Not saying that to be mean, I mean I've had wool pulled over my eyes a few times.
"I’m not expecting to grow flowers in a desert, but I can live and breathe and see the sun in wintertime"
Check out my stuff!
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#3
Seems to me that there is too much drama on both sides of the fence.

Neither friendships nor relationships are about talking. They are about doing.

I think the proverb that applies is, "Shit or get off the pot."
I bid NO Trump!
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#4
Any relationship that involves money should ring alarm bells.
"You can be young without money but you can't be old without money"
Maggie the Cat from "Cat on a Hot Tin Roof." by Tennessee Williams
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#5
LONDONER Wrote:Any relationship that involves money should ring alarm bells.

Unfortunately true... I mean if anything it is a battle royale on who's buying dinner -- if anything it should be like that.

But when someone is staying around just because you're buying them things is down right manipulative and abusive.

I couldn't imagine doing anything like this to someone. Heck I feel bad for not buying dinner...
"I’m not expecting to grow flowers in a desert, but I can live and breathe and see the sun in wintertime"
Check out my stuff!
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