First time posting here and I'm not really sure if this belongs here or if this is more suited for /r/relationships, but here it goes.

I have a friend, Mike, who I've known for 4 years. Mike is 28, has a stable job, and a nice personality (among his guy friends anyways). Mike is also fairly short and very overweight, and not exactly good looking. For as long as I've known him, he has never had a girlfriend (although he claims to have droves of women lining up at his door).

I fortunately haven't had trouble with women since I was about 14, and I have been in a stable relationship for the past 8 years. That said, I do enjoy the chase, and I occasionally toy with meeting new women, even though I never take it far and usually end up getting intentionally friend-zoned so to speak. I still hang out with these girls, and often invite them out and introduce them to my friends, which has lead to several of them getting together, but never Mike.

The thing with Mike is his MO sucks: within the first 30 minutes of meeting a new girl he is asking for her number. He behaves well at the get-together, not being too clingy or anything, and acts his normal self. Later at night, he usually starts texting them, and continues to do so for a while. The problem is that Mikes tries to seduce women "like it's the 1930s" as my friend Rob like's to put it. This is the way these texts go:

  • Mike: "Hi beautiful, how are you doing this morning?"
  • Girl: "Hey, I'm good, u?"
  • M: "I'm good, thanks, I just wanted to let you know that you looked gorgeous last night"
  • G: "Thanks"

..... next day ..... (this is real, taken from a screenshot one of these girls sent me)

  • M: "You are a the perfect girl, you know?"
  • M: "Really, you've got it all"
  • M: "You are beautiful, charming, sweet, intelligent, hardworking and happy"
  • M: "That's perfection to me"
  • G: "Oh, thanks!"
  • M: "You are the first woman I meet that is like this"

.... You get the point. This happens with every girl I introduce him to. I usually get a text from the girl saying: "Your friend Mike is insane, I'm gonna block him"

My friend Rob and I want to help him. Mike is a decent guy, he doesn't have the looks, but he has the right personality. We feel he has two problems: Chasing girls who are way out of his league. Mike doesn't like overweight girls, or girls who are not all that good looking. He sucks at going after them, he is way too intense and scares them away almost immediately.

Rob and I have tried to talk to him about this, but we really haven't found a way to convince him he is scaring them away.

Any thoughts on how we could help him?

TLDR: My friend Mike scares away women by being way to intense. He won't listen to reason. Any suggestions?