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Get his name above your ass in Chinese characters. Add a couple nautical stars and a Celtic Winnie the Pooh while you’re at it. Then, offer to show it off to him on a sleepover date. At your parents' house.

Or not.

I’m a firm believer that you can date the professionally undateable. I wouldn’t believe it myself if not for the fact that, many moons ago, I successfully picked up a bartender.

A favorable outcome rests on a combination of your target being attracted to you, your target being available, and you not being intimidated by your target. You can't control two out of the three, but take comfort in this. Your heart doesn't palpitate every time you run a yellow light or scratch off a lotto ticket. Very little of this rests on what you say or do.

Just find that proverbial "in." Ask him about the band on his shirt (because I know there is one) or where he got the delicious-looking sandwich he’s eating. Schedule an appointment near closing time, bring along that friend, and loudly mention eight or ten times that you’ll be grabbing a drink in the immediate vicinity. There’s nothing more simple and effective than a casual "come with?" If he declines the invitation — either because he’s caught off-guard, is not into you, has plans to leave the country, etc. — simply leave your contact info on one of those business cards he keeps on his desk. The follow-up paper exchange is important. It gives the person time to think and make an honest, non-pressured decision. It also gives you time to agonize, but let’s try to focus on the positive.

I recommend giving out a phone number and email address when you’re the one initiating. Yes, it looks a touch desperate, but if he’s as phone-phobic as I am, an email option can be a game-changer. I have a guy friend who put off calling a girl for close to three weeks. Imagine how much faster he would have moved if he could've hidden behind his Gmail.

You are cool. He’s just some mofo who works in a tattoo parlor. Ask him out. If he says no, you’ll be still be you. Only that much braver.

Dear Restless in Singleville,

You’re coming on too strong. That, or you’re being too mercenary with your dating. Try a drink instead of dinner and a movie. If you’re not into booze, then coffee or ice cream. Contact her post-date to let her know you had a good time and would like to do it again, but put her in charge of making the next plans. It sounds like you’re whipping out your Blackberry and blocking out Date #2 before Date #1 has even ended. Give it a day or two; allow breathing space. Ask your BFF who’s not interested to audit your personal ad — photos, username, the whole shebang. Bribe her with a free dinner in exchange for five honest criticisms, with a jalapeno-popper bonus if she gets a second opinion from a female friend. If she won’t do it, ask a relative or one of your married dudes.

What about those liberal ideals? Is there any chance you’re being an asshole about them? I’ve known people who can manage to make my most deeply held beliefs sound unattractive. Try not talking liberal smack on dates, and eliminate all the NPR references from your profile. Trust that like-minded people attract like-minded people, and even if they don’t, sexual attraction shall overcome all obstacles.

When I said that you might be too "mercenary," I didn’t mean to "relax" or "just let it happen" or any of that cock-and-bull that people who haven’t been on a date in years try to sell you. Keep going on dates and keep looking for your future missus. Just don't expect everything to be linear, or that you will be rewarded for good behavior. Sometimes good people stay single. For a long time. It sucks, but what’s the alternative?

You mention moving. It doesn't sound like you’re serious, but here are a few ideas to tempt you, anyway. Moving is awesome. I’m a big fan. It expands your pool of applicants and beats the hell out of long-distance dating.

Dear The Giver,

Bea Arthur forgive me if I’m wrong, but I smell a hoax letter.

You date this woman for four months before inquiring as to whether she’s ever gotten off, yet you were "more than willing" to "take care" of her? What were you doing all that time? Changing her feeding tube? Giving her a French manicure?

She’s too shy to talk about orgasms or buy her own sex toys, but now she’s a vibrator-wielding maniac? She goes from silently never climaxing, to being bossy and vocal? Sorry, I don’t buy that. It sounds to me like you’ve got a bone to pick with plastic boners, or you get off on not being able to come and want to share your love of blue balls.

On the other hand, your fake question is twenty-percent more plausible than all the other fakers, and it’s nowhere near as braggy — "I can orgasm while waiting for my prescriptions!" "Help! My girlfriend is ADDICTED to my enormous penis!" — so I’ll take the chance and ask my always-knowledgeable readers to field this.

Should The Giver let his girlfriend’s Rabbit obsession run its course, or should he boil that sucker à la Fatal Attraction? Gang, why are some of you so weirded out by the most basic of sex toys? I've been around the block or four, and have yet to meet a guy who greets a vibrator with anything other than veiled indifference. Then again, I’ve never had a Fleshlight pulled on me, either. Maybe it’s different when your genitals are the ones being replicated?