How do I get close to him?

[ShiftyNJ]

If I knew that my roommate had a crush on someone, I'd be strictly hands-off with that guy no matter if I was attracted to him or not. Also, the age difference may not bother you, but it might bother him.

I agree with John and the others, you need to simply ask him out and see what his response is.

[MENTION=22470]Pyromancer[/MENTION] raises a good point; go easy on the flatmate a.) you may be unintentionally leading him on by suddenly accepting his invites and b.) the way you let him down could impact how they collectively decide how to deal with you. If he still sees you as a nice guy he may be okay with the one you like pursuing something with you, but if he thinks you're a prick, he may discourage it. and c.) golden rule. How would you feel if you were him?

Best of luck.

[Bowyn Aerrow]

He is an introvert - which means that he will either be leaning up and holding up a wall in the party scene, or studiously examining his glass and pondering the deeper meaning of life in the universe at the bar.

It does not help that you keep on going over to his place to visit and be with his roommate. We have rules in our society which most introverts are painfully aware of, one of them is to not make a move on your roommates love interest.

In order to 'fix' this, you need to come clean with the roommate and stop using him as a means to an end.

Secondly, you need to stop hinting at shit and come directly right out and tell this fella what it is you want. Unfortunately most introverts are poorly educated in social graces and hints and all of that stuff. Many have no idea a guy is interested in them until the guy grabs them and plants a kiss directly on their lips - some still don't connect this with 'interest' and thinks perhaps this kiss was an accident.

Since he hasn't dated anyone at the bar/club - I can assure you he pretty much has written off any male at the club/bar scene to be a drunk/druggy/dancing queen/sex addict and is only there attempting to be social because society insisted that people must do these sorts of activities to be 'normal'.

No doubt hope spring eternal, and somewhere inside of him he hopes that one day his prince charming will walk into the bar and break the common chain of what most guys are at the bar for.

The day will come (and soon since he is 30) where he will give up on the bar scene and walk away and never return.

So this window of opportunity may be closing - forever.