The macho thing has to stop because it is an act. The too nice thing has to stop too. He needs to focus on giving her a fun experience before buying her gifts or getting to cute with his words.

He needs to get some hobbies too. I know he is still young, but it will help him out allot. He can gain allot of confidence from other activities and carry it over to his dating life.

His belief that he is failing is maybe his biggest problem. I might have to write a future blog post on it.

I dunno bout dating more than one girl at a time, he does wrap himself around her finger too fast, but having multiple-girlfriends might not help the situation. I do agree however, that he needs to not focus all of his attention into women, but he doesn’t have much to focus on. He’s 19, a super-super-senior in High School and doesn’t really have a job.

Unfortunately I don’t think you get what I mean by the tough guy image. He is honestly a shy, self-loathing, kind, gentle, and sweet guy. But to protect himself from being hurt he emanates this persona of a tough-macho-dude. When a girl falls in love with that persona he shows to the public, she gets disappointed when she finds out his private persona of a gentleman. Usually staying with him until she finds someone better. You are right that he changes, but he doesn’t put the nice guy image on, he shows who he really is.

I am very grateful as always of your input, but I think you misunderstood what I meant in regards to him. He DOES NOT have a girlfriend and has problems talking with girls because he believes he is always failing.

I will try to help him do as you suggested and not spoil the girl rotten the second she says “I like you”, he should buy her stuff but only if he gets something honest in return. So far I can see that he buys a girl stuff in hopes of keeping her as his girlfriend. The gold-digger problem. He is a very charming and sweet guy when it comes to his words but as you have mentioned before he is TOO nice and gets walked on.

Thanks again!

One of the things your friend needs to do is date more then one woman at a time. He is putting too much of his feelings into one woman too fast. Thats one way to stop becoming overly attached to a woman too soon. You also need to be busy with your hobbies, dreams, and goals. Dating is only one part of your life.

It sounds like once a woman is attracted to him he tries to rush things into a relationship. Once he does this he puts on the nice guy image. In other words he changes. She doesn’t like those changes. Those changes are not congruent with the first impression that she got from him.

Your friend might want to try qualifying women so that he is more likely to get what he wants.
He can do this by making statements and seeing how she responds.

If he likes women who cuddle then he can say something like this.

“I like women who like to lay around and cuddle.”

Then you see how she responds to that statement. If she doesn’t meet some of his needs then he will need to date more women.

My buddy is a tough guy and I think all the girls he dated wanted that tough guy image and when they found a nice guy underneath they split because the illusion was gone, how should I advise him that all the girls he dated wanted his image and how to help him find a girl that is not looking for his image but who he really is?
- Kenji