This is all games and manipulations. Why not just ask Bobby to tell Susie to tell Johnny to tell Beth to ask this guy if he likes you. Or have you already graduated high school?
You want him? Ask him out. No chasing him. No games. Just walk up to him and ask him if he’d like to have dinner with you. Some people would suggest you do it after work to help separate the office and social aspects of the relationship. Your call there.

If you’re going to wait for him to ask you out then there’s a few things you should do to prepare.
First, clear your fingers of jewelry. Make sure there’s nothing there that he might mistake for a wedding or engagement ring. I’ve missed more than one opportunity to misleading rings. Playboy quality babes, too.
Second, along those same lines you’ll want to review any pictures on your desk. Remove any pictures of men roughly your age who might be mistaken for your significant other.
Third, some women make sure to mention their S.O. in casual conversation to make it clear they’re off the market. Some similar remarks about how single you are might help. Disasterous dates, the movie you went to see all by yourself, etc. If you’re gonna drop hints make them Hiroshima quality hints.
Fourth, any excuse you can find to hang around his cubicle helps. He might figure out that you’re interested and it gives him plenty of opportunity to ask you out.

Good luck.

I agree with DCB in that women instinctly perfer to play a more passive role and let the man be the aggressor. If a man will not strongly chase a woman he is attracted to, it speaks to his confidence, both with respect to women and in life more generally. Having been a guy who once couldn’t assertively approach women and then becoming a guy who could, I can assure you this is very true. On a more subtle level, the proper energy polarity is established when men assume a more assertive role (see David Deida).

One extra factor though worthy of consideration is that he may follow the rule I mentioned the other day: no neighbors or coworkers. So he could be a real alpha male and be willing to flirt dangerously, but perfer not to get his girls from work due to professional awkwardness.

Bow to your sensai

Cobra Kai writes, In a similar vein to the office mate post, I have a small crush on my Sensai at jiu-jitsu class. He is my age, cu […]