He Notices When I Notice. Help!

Q: I've just finished your book and I need to know how I can apply your techniques to my current situation. There is this guy at my job that I think is cute and I'm interested in but given the fact that we work together and he's kind of quiet, I'm not sure how to do the whole "non-approach" approach that you discussed throughout your book. To make matters worse, a couple of times when he got a hair cut I complimented him and told him he looked nice (including today); he usually just says "thank you" but today he said "you always notice." So, now he notices when I notice his haircuts (to be fair to myself, I notice everyone's new hairstyle/cut---I'm an observant person). Is it too late to put your techniques into effect? Can this situation be redeemed? Can I gain the upper hand? Help! - Stephanie

A: The situation is definitely redeemable. I would take his noticing you noticing him a positive, actually. It's flattering to have someone notice small changes in your appearance, and he wouldn't have said anything if he wasn't flattered (regardless of what he sounded like when he said it). I would make a point of letting him hear you compliment someone else on a change in their appearance to let it be known that he's not the only one you pay attention to. This will put you on neutral ground again, if you're not already doing this.

Then, I would go into one of the more chatty openers the next time it's appropriate - maybe when he's waiting for the elevator, or at lunch. My suggestion is to pretend to get a voicemail from your friend at the exact moment you're near him, and then say, "Can I ask you a quick question? My girlfriends and I need a guy opinion. My friend Julie went out with this guy last week, they had a great time, and he just called her and said "See you around". What does that mean, in guy-speak? Is he interested?" Keep it low-key, kind of funny and cool. Make sure it's clear you didn't seek him out to ask the question, but rather he just "happened" to be the guy closest to you when you had a guy question. From there, you can morph into "What are you up to this weekend" talk to establish a connection with him. Since he's shy, he may not take the bait and ask you out, so you could organize a small-ish group to go to happy hour after work sometime soon and invite him. Once he's there (out of the work environment), you can start to flirt a bit. I bet he'll respond.

Good luck! I hope it goes well.

If you have a question, feel free to email me at sam@screwcupidthebook.com. I'd love to hear from you!