My ex-bestfriend's lover wants to date me

[Belovednikki]

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 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?

[Knight2001]

hi,

you're not in to him, so don't date him.

you don't find him attractive, so don't date him.

don't date him, it's pointless.

[nuttybuddy]

Obligated to date him? That’s a strange thing to say. You should think about that because that already tells you your TRUE FEELINGS. You should not be guilt-tripped into dating a man. Plus this guy has loads of baggage. Two baby mamas??? He’s one smoooooth talker. You don’t think he used those same lines to pick those girls up? Stop fooling yourself. He’s a flirt and always will be. Your #2 reason has RED FLAGS ALLLLLLLL OVER IT. Pay attention to what your mind is telling you. Your heart will follow suit. Don’t let this guy trick you to be the third baby mama and leave you high and dry. A real gentleman would not have left the first baby mama.

[Belovednikki]

Obligated to date him? That’s a strange thing to say.

 

It's very weird. But I hardly get a chance to date so when a half way decent guy comes my way (once every few years) I automatically think he might be THE ONE. But then I start picking out all the things I don't like about him and subconsciously run him away and then I'm left feeling bad and alone. So here comes this guy saying all the right things that I've been praying for but he's tainted. So now I'm picking out all the things that I don't like about him, when maybe I should ignore it and go ahead and just date him because I have nothing going on. BUT I CANT! All my friends say that I'm tripping and I should go ahead and date him (probably because I stay single) but I can't ignore these red flags. I just want to make sure I'm not the one tripping.

[Belovednikki]

Yeah you're right!

[Clio]

 

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.

 

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.

 

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?

 

 

There are some glaring RED flags in your post. Imo, you should pay attention to your gut instinct. This guy sounds immature (2 kids by 2 different mothers. Both relationships failed. At 45+ he left someone more than half his age and barely of drinking age pregnant.) This guy sounds like someone who never grew up and who uses his persistence, sweet talk, money and status to lure women who don't know any better. Past behavior is indication of future behaviour. Overall, I can't see this ending up well for you. The guy sounds like a player. Not having dated in years does not sound like a good reason to go for a player whom you don't even like to begin with. His money, status, persistence, sweet talk are not valid foundations for a healthy relationship and the guy clearly has a long history of very bad life choices when it comes to women.

 

P.S. Your description of him is NOT what a half decent guy looks like. See again your point no.7. At 45+, the guy has not even grasped the basic concept of using condoms.

[Belovednikki]

There are some glaring RED flags in your post.

 

P.S. Your description of him is NOT what a half decent guy looks like. See again your point no.7. At 45+, the guy has not even grasped the basic concept of using condoms.

 

Yes!! You are 100% correct and on point. I just couldn't for the life of me figure out why my friends were like GO FOR IT!! I thought I was over looking a quality that single girls aren't usually privy to. Thank you for your insight!