A few months ago a really good friend of mine passed away. I was cool with his best friend so I would text him from time to time to see how he's doing. Two weekends ago he hit me up and said he was in the city and asked if I wanted to grab a drink. I wasn't doing shit so he came and swooped me up. While out sipping my favorite Japanese whiskey he professed his feelings for me and asked if I would be interested in dating him. The catch is, in 2015 he "dated" my at the time best friend. We fell out this summer because I made a comment behind her back saying that she isn't the type of person you should leave around your man. My ex friend is very loose and I was tired of it and her. So yeah I said it and the person went right back to her and told her. While they dated she lived overseas so they saw each other three times that year but they had a lot of cyber sex and had a lot of stimulating conversations. She really liked him. She was ready to move home to be with him. The dude seems real cool and I can tell he would spoil me which is something I have never experienced from a man before in my life. Here are my issues:
1. I have never looked at him in any way other than a friend. I don't find him attractive but he's really nice.
2. He had sex with my friend (possibly raw) but he claims that even though they had sex he never was into her like that and he has always wanted to date me.
3. This girl and I are no longer friends and we will never be friends again.
4. I haven't dated in YEARS!!!!!!!! Years.
5. He claims she wasn't honest with me on the type of relationship they had. He feels she should not be included in my decision to date him.
6. He is really into me. He texts me all the time and uses emojis that would be cool if I was into him, but I'm not so it's weird to me. He's always trying to see me and do nice things for me but I stop it because of all the circumstances.
7. Two baby momma's and two kids. One of his BM's is 22 and he's 47.
8. He's very well established.
I could go on and on with little petty reasons that I would not be privy to if he hadn't "dated" my best friend. Being that I haven't dated in a long time and don't usually get guys that want to date me I feel obligated to date him and I feel guilty when I resist him. He has everything I want in a man but he's tainted. All In all I'm not attracted to him but I feel so bad rejecting him.
What do do I do? Date or don't date?
IMHO - this is not a road you should go down.
This guy's got too much baggage.
Why haven't you dated in years?
That's a good question. I definitely want to date but the situation never ends in my favor. Guys can't really give me a straight or honest answer of why they don't want to date me.