Feel im not in his league

Believe in yourself. If you're having nice dates go with it. His ex is his ex for a reason. You and he have a mutual attraction if you're having nice dates, so you must both see something attractive in eachother.

Sounds controlling after a few times meeting.

II do wear too much at times he said i look better with less makeup - that's a compliment IMO. Personally, I wouldn't be a fan of makeup and I see some women and think, why are you wearing so much, you don't need it. I don't think that this is controlling behaviour, it's an observation and if it was said in a nice way, I would see that as him being comfortable with you.

He talks alot about ecx wife and calls her "the slut" - that's not good, perhaps get the back story. If she cheated on him and he was really hurt, I could understand, but I also feel that people say too much and some things are best left unsaid.

both his exs are friends on facebook and making him feel like he is bad - men and women can be vicious. If he was with 2 friends they could be ganging up and being nasty… or he could have been horrible to them and deserves the criticism.

his closest friend is a 20 year old bi curious girl he is 40 i find that stange and he socialise with her often - Has he indicated that he has feelings for her… does she have feelings for him? Men and women can be friends - I have many women friends and I have no desire to sleep with them. Some are in their 20's and I'm in my 40's. We just have shared interests. They're not my closest friends as they've been my friends since my teenage years. I agree it's odd that his closest friend is so much younger, and female. Perhaps there is a reason for this - Is he foreign and this friend is from his home country? Do they share a mutual interest? My advice would be to find out more.

Regarding your original post about feeling out of his league. Perhaps he was a bit of a player and wants to settle down now. Maybe being with younger attractive women is not what he wants anymore - as you get older, your wants and needs change a lot. Younger women may want to have kids and he may not.

I met my wife in my late 20's and some of her friends warned her off because they thought I was a player. I wasn't, I just hadn't met the right woman and we're together 20 years now, and those friends have completely done a U-turn. I hold no grudge; I respect them because in their own way, they were looking out for my wife. What I love most about my wife is that she doesn't pretend to be anyone. She is naturally beautiful but never felt the need to chase attention. She was very comfortable with herself and that was very attractive.

If you're wary, play it slow and see how it pans out. I think everyone deserves a chance but it's up to you :-)

Not a good sign

The thin end of the wedge i reckon

His attitude towards his ex is the major alarm bell for me here. Even if she did treat him badly, there is something off about a man referring to another woman as a slut to someone he barely knows. You are not his therapist and he should not be using dates to off load his anger/frustration/sadness/whatever about the breakdown of his relationship. The make up thing is possibly controlling/possibly a compliment - hard to know without context but the comment on his ex is a worry.

Move on. It sounds like you're just dazzled by his looks.

OP, do you see him during weekends? How did you see pics of his ex and his friend?

If you feel so bad about your looks why do you go after attractive men? BTW he might be from an attractive nation, so he might be average in his own country. And he might be ugly inside…

Just enjoy yourself.

If it doesn't work out, you'll find someone else. Heartbreak won't kill you. You'll bounce back in a couple of months.

Nothing to fear.