I (late 20s, F) have a friend (late 30s, M) who I've fallen pretty hard for. I think we're pretty good friends considering we've known eachother a little less than a year. I feel like we sort of gravitated towards eachother pretty quickly. I was pretty smitten with him from the moment we met, and I've always thought maybe it's mutual but he hasn't made a move so I'm always doubting.
This friend is very well off and has helped me out a great deal financially. I personally think that even if the amount of money is not of consequence to the giver, anyone would agree the amount he's given me is significant. To be clear, it's never "fun money" or "just because," it has been to help me pay off debt and then more recently, help with rent because I lost my job and haven't found another one yet. It is by no means a "sugar daddy" kinda scenario because there's absolutely zero sugar involved.
This is where it gets tricky for me mentally, because I have pretty strong feelings for him, and I have had these feelings since well before he ever gave me a cent. I never expected him to give me money nor have I ever asked for it. I was really uncomfortable accepting at first and it took a lot of convincing, but to be honest, i'd have been screwed without him. He has always made it clear that I don't owe him anything in return, and I know he's sincere. But the problem is, *I* want more out of our relationship, but it feels like the money thing makes that weird. How can I ask for more when he's already giving me so much? I worry he'd conclude that I've grown these feelings of affection for him just as a result of the comfort/safety he's offered me through financial means. I am so grateful, of course, but I'd love him even if he didn't have any of that. I worry he wouldn't believe me. I feel like a pathetic loser, having to rely on a man's money to survive, especially when that man is not even my man. He isn't just paying my way through life though, he knows I'm trying really hard to find another job and get back on my feet and he's encouraging. He has hinted at paying for more things I need/want, and some of these are things that I would feel completely fine with a partner paying for, but a man who I'm not in a relationship with… it just feels wrong and weird? When you're in a partnership, the more financially well off partner supporting their partner's goals financially just makes sense, it's like investing in "us," but for a man i'm not in a relationship with to do that… it's too much.
The thing is, I absolutely can't say to him "I'd only be okay with you paying for that if you were dating me," because that sounds straight up manipulative and almost predatory. I should just be grateful for what i'm given, right? But I think other women could understand where i'm coming from here. If he offers to pay for something and I tell him no, he's not going to understand why and he's going to ask me to explain. He's someone I really care about, so I feel like he deserves an explanation, but I'm just not sure how to explain in a way that doesn't come off wrongly?
As far as where we're at in our "situationship" if I can even call it that, I feel like it's flirty but… mildly. He never, ever makes comments about my appearance, good or bad, save for the once or twice he's pointed out that my hair is different lol. While that might just be him trying to be a good, respectful guy, i'm just not used to men being that…. wary, if they're into it. They usually step a little over the line, testing the waters. Aside from that, he started opening up to me pretty quickly in a way he apparently doesn't with others. We also have talked at great lengths about how we view relationships, what we want out of life, our morals/values, etc., and have found we agree on a lot of things. I also think he's seemingly comfortable touching in a way people who are not in a relationship would usually avoid? I'm talking things like, legs and arms touching while sitting together and not making an effort to move, leaning in really close and practically leaning on me to say something, that sort of thing. We always end up together when we're in a group setting, but maybe i'm just a really good friend to him, I don't know. He's very thoughtful, usually remembers things I say offhand and has given me a few nice small gifts based on things I've said. There are more things that I think are signs but I think they're too specific and I worry someone I know will come across this somehow lol.
I have mulled it over so many times and struggle to understand why he wouldn't make a move *if* he was interested, which then makes me think he must not be… but then when I try to tell myself he's not at all, that doesn't make sense based on his behavior either. My friends all seem to agree he's clearly interested, but I think he's a really unusual guy and so hard to read so I can never be sure. It feels like I can't be the one to broach the subject of feelings because of the power dynamic and the money stuff.
What do you think? What would you do in this situation? Any advice?
TL;DR – I have feelings for a friend who is well off and helping me financially, feel like our relationship is stuck in a weird place and don't know how/if I should attempt to progress things further