Tongue-tied

Dear Dr.Lovemonkey,

I do not have trouble talking to other people once there’s an established context for our conversation. I am not good, however, at creating these contexts on my own. This is a problem, because as a testosterone-driven college guy I suffer from chronic attacks of severe infatuation. As I sit typing this letter to you, I’m casting more than a few surreptitious glances at a fellow sitting at a computer just ahead of me and a little to my left. I’ve scoped this fellow out more than once, but I’ve had an extraordinarily hard time trying to think of a reason to start a conversation with him. The problem is that there’s absolutely no context from which to start. I’ve had the same problem recently in a local bakery that I visit frequently. This one waitress behind the counter always attracts my attention, but I have no idea how to say, "God, You’re gorgeous!" without sounding just a bit sorry-assed. Can you recommend any strategies for approaching total strangers? I’m sick of being infatuated from afar.

— Sick

Dear Sick,

Everyone has their own style when it comes to formulating conversations out of whole cloth. As you seem to have intuited, rushing up to someone and declaring, "God, you’re gorgeous," is generally bad form. One reason is because this is usually a dead end. I mean, how does one respond to such a declaration? Also, it has the ring of the primitive come-on to it.

If one wishes to master the art of oblique small talk, one should be observant of oblique and small things. Let’s say you’re in the library, ogling that fellow at the nearby computer, and he’s wearing something unique, like a "Wendell Wilkie for President" button. This would be the signal to rush off to the stacks to bone up on the Barefoot Boy from Wall Street, so that you might later bone up on the object of your affection.

Assuming your favorite waitress is in the process of serving something to eat or drink, you could spark up a conversation having to do with the wide world of food and beverage. Obviously, a stereotypical lounge lizard come-on like, "I’d like to have a ‘Sex on the Beach’ " (a cocktail apparently dreamed up for just such low-grade encounters) would be strictly taboo. Dr. Lovemonkey is thinking more of something along the lines of, "Did you know that the Aleutians consider meat loaf a sacrament, to be consumed only with a 12-ounce Diet Rite Cola?"

Blurting out something so transparently desultory (and stupid) may indicate to the waitress that you are a fun-loving kind of a guy. Likewise, it may also show that you are a moron, but these are the inherent risks in attempting to subtly hit on another individual.

Take heart, however. Judging from your letter, Dr. Lovemonkey ascertains that you are bisexual (the "fellow" and the "waitress"). This means that you are open to potential romance with the vast sea of humanity. As Woody Allen observed, being bi doubles your chances of getting a date on Saturday night.

Dear Dr. Lovemonkey,

My best friend broke up with his girlfriend a couple of months ago, and since I have always had a thing about her, I’m thinking about asking her out. I’m concerned that he might get pissed, even though they are now pretty angry at each other. What should I do?

— Up In the Air

Dear Up,

If this is really your best friend, discuss it with him before you do anything. Get a sense of how he feels. He might have strong feelings about this, and, of course, maybe he’ll deny it. You’ve got to be able to read his feelings to an extent. If you sense that he’s uneasy with the idea, you might want to back off, because this could, indeed, jeopardize your friendship.

Send questions and romantic quandaries to RUDYCHEEKS@prodigy.net