Found out we’re VERY mismatched financially

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    singleagain1987
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    I’m going through a very friendly divorce. We got married young and have realized thay while we’re great friends, we’re not really interested in each other in ‘that way’ anymore. Because the relationship aspect of our marriage has been gone for so long, we decided that we’re both ready to see other people. I’ve been in LTRs since I started dating… Never really ‘played the field’.
    I met a guy at work and he’s gorgeous. He’s always been really friendly with me and we clicked right off the bat. I work in the restaurant business and so does he, so I assumed we were on a similar playing field. We started hooking up as FWB and I made him pinky swear not to fall for me, as I’m kind of all over the place emotionally right now and I really just needed some rebound . He said that wouldn’t be a problem. He’s the smooth, muscular and polished type. I’m tattooed, size 12, tomboyish and snarky type. I’m very attractive and so is he, but complete opposites. I was very surprised initially when he tried to pick me up, as we are so very different and he’s not the type who usually goes for a girl like me.
    Most people at work know that I’m married but separated. I have started referring to my guy as “my guy” because ‘ex’ doesn’t seem right and neither does ‘husband’. We still hang out as friends a lot. I assumed that he knew that I was married. After we hooked up, he made a comment about how he knew I was on-again-off-again and was okay with that, but could never sleep with a woman who was either still married or engaged. Awkward. I didn’t have the balls to say anything then… I just kind of nodded. Later that night, I called him and explained my situation and apologized if I accidentally misled him, but I had no idea he didn’t know. We’d already slept together, so the damage had been done, but he made sure that my guy was 100% okay with me seeing other people and that I wasnt doing anything behind his back.
    The was good, so we continued seeing each other. I’d get the random “let’s hook up” texts, just like a typical fwb situation. He started talking to me about an investment opportunity he was thinking about getting involved in. It seemed pricey, so I asked how much it would cost and he shrugged, “only about 100k.” I asked him if he was planning on taking out a loan for the start-up and thats when he explained to me that he’s an heir and worth millions. He works because he enjoys it, but really doesn’t have to. In retrospect, it’s kinda obvious. He’s very polished, has the mannerisms of somebody who comes from money, and dresses very well. I just assumed his parents or grandparents were wealthy and he was spoiled, never did I imagine that one of my coworkers was a millionaire.
    We continued hooking up. The last time we hooked up, after we finished, he held my face and kissed my forehead without a word. He’s never done that before, and it oddly felt more intimate than the making out or even the . I don’t like quickies… I always feel like a bit of a afterwards, but he was on his way to meet his friends and I really wanted some. We talked for about an hour, even though it was supposed to just be a quickie. After he left, he called me as he walked out the door and chatted with me all the way to the restaurant. I asked him if he was late and he said, “very, but I don’t want you to feel like a .” After that situation, he’s called me a few times to talk about work and personal things.. like a friend calls a friend, not an fwb.
    Anyway, there’s a movie coming out soon that I really want to see, but don’t want to see alone. I didn’t feel he and I should start going on dates because its hard to keep a situation like this casual. So I shot him a text and told him that I think I’m ready to start dating again and asked if he’d rather me keep it to myself when I start dating or if he wants me to be open with him about it. He didn’t text me back. That night, he pulled me aside after work and explained that he really wanted me to consider dating him.
    My problem is this: if I didn’t know about the money, I’d be very happy. Every girl we work with wants to be with him, he and I click really well, and the is great. I like to pull my own weight in a relationship… If we go out on a date, I pay half and if we go on a trip, I’ll pay for the hotel and let him pay for gas, etc. My problem is that when he goes out to dinner, he goes places like Ruths Chris and when he goes on trips, its weeks in Times Square or Tahiti. I work in a restaurant. I’d never be able pull my weight on those types of outings and he would never expect me to. I don’t know that I’m okay with being in a relationship where he’s so far out of my league financially that I can’t pull my own weight.
    I think he really likes me and I like him, but $ makes it awkward.
    I know guys with that kind of money are usually involved with the supermodel type. I’m really not that type nor can I compete with that type in a purely physical sense. There have been a few different times at work that I’ve had his back and stood behind him when people started talking shit about him. I’m a sweet girl and I’d do it for any one of my friends. He always seems shocked when it happens, so I’m guessing he’s unaccustomed to genuine people who genuinely care about their friends. I think that’s more what this is than anything. Ive volunteered most of my life and come from a well below poverty level family, so I’m as down to earth as they come. I think he’s more drawn to who I am as a person than the physical side of things, but like I said… I never played the field. I know he has all the right tools to be a player: the money, looks and charm. Do you think he’s just playing me or genuinely likes me? Also, how would you handle the money situation? I’m kinda viewing it as a dealbreaker and I feel horrible for it. I’d never judge somebody for having too little money, but I know I’m judging him for having too much. I like him a lot but I guess I’m too proud to be a mooch and too scared to be played.

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