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He may have told his friends to approach you because he wanted them to report back to him about what they thought of your personality.
He may be the kind of guy who finds it easy to flirt and make sexual jokes with many women when there are no romantic intentions involved.
In essence, he can be himself around them because there are really no stakes.
However, when there is a woman that he is actually interested in romantically and has invested some time thinking about, he could second-guess himself.
As a result, he won’t approach her and may choose to send his friends instead to help him figure the girl out.
You could be that girl to him.
Flirting with every woman around you, making a lot of sexual jokes, making fun of some women in a joking way, talking about sex a lot, showing off, bragging about the women that are in his huge social life, drinking and using drugs are all indicators of how he would behave if he were to become a significant other to you or anyone else.
You are the only one who can judge if these are behaviors that you are able to tolerate or not.
If you don’t feel that you would be able to tolerate them, it may be best to look at them as red flags and avoid giving him a shot.
Try not to make the mistake of thinking that you can change this guy if you were to give him a shot.
The likelihood of that happening is incredibly slim and only tends to happen when you get a guy to a point where the value of his relationship with you is much greater than everything else.
Getting a guy with this much social clout and influence to that point is incredibly difficult and typically comes with a heavy emotional toll.