The Source: Jack of Diamonds, Pick Up Artist

The Dilemma: There are breasts in front of you. Breasts that you'd like to touch. If only there was a step-by-step protocol.

The Advice: I always thought you did some over-the-shirt, then under-the-shirt, and then no shirt, but apparently it's much more involved. Watch as Py Kim, an amiable, if a touch hyperactive, version of Dr. Ruth, complicates the uncomplicated with Jack of Diamonds, a self-proclaimed pick-up artist who looks as if he's dressed to sell ShamWows. A lot of the talk focuses on powering through your target's hesitation and getting her to say yes when she wants to say no. Watch for the Karate Kid "wax-on, wax-off" shout-out at 3:47.

The Rebuttal: Instead of treating sex as stratagem, why not relax and be in the moment? The best education you get is the one you get from your partner. Listen, learn, and respond, kiddos. It's one-on-one tutoring at its most effective. Boob-touching, while fun, isn't a game to win, and if you win against a reluctant opponent, it's not really winning at all.

The Source: Dear Uncle Mat, San Antonio Current

The Dilemma: "I have been having a casual affair with a classmate since the beginning of this semester…He is very attractive and nice, but just not the type of guy I want a relationship with…I liked our arrangement because it was clean and easy and keeps me satisfied but not distracted from my goals. He hasn't admitted he wants more, but it is becoming painfully clear…How do I tell him to back off without hurting his feelings or losing the good thing I thought we had going here?"

The Advice: "Unless there is something horribly defective with him, I suggest trying dinner or a movie. Maybe he is more than you think, and relationships are not always distractions…You'll have to be direct and let him know you want to keep it to just the sex…But you might consider whether you are using your educational career as an excuse to avoid a relationship for other, more personal reasons...I understand that there can be an indefinable something that makes a guy not the one for you, but it seems strange that you would still want to keep sleeping with him."

The Rebuttal: She already said why she doesn't want him — he's fun for a lay but not the type of guy she sees herself with long-term. "It seems strange that you would still want to keep sleeping with him." Oh yeah: because great, strings-free sex has never in human history been a draw. I would ignore Uncle Mat's advice to go on a date and just cut the poor guy loose. Being friends with benefits isn't fun anymore when the affection grows lopsided.

The Source: David DeAngelo, Ask Men

The Dilemma: "There is this girl I like at my bank and who I thought liked me…I used some charm by dropping a card through the drive-through with a note asking if she wanted to go out Sunday night…She told me to give her my number and that she would call me for Sunday night. Well, Sunday rolled around and she didn't call, but the next time I saw her she turned red and greeted me with a smile and the apologetic excuse that she was away that weekend and she felt so bad she didn't call me...It's been a month, but I see her about three times a week at the bank…My gut feeling is to move on."

The Advice: "Here's what I'd do if I were you: next time you see her, say: 'OK, you're playing hard-to-get, but it's not working on me.' (Say it in a funny way.) 'Give me your e-mail and number, and I'll call you in a few days.' Then get her info, and wait a few days to call her. When you do reach her, tell her that she owes you a cup of tea for being flaky. And make her pay for it."

The Rebuttal: Here's what I'd do if I were you: change banks. You might get a better interest rate and the invaluable benefit of no longer looking like a stalker. (Who visits a bank three times a week, in person? Don't you have an ATM card?) Listen to your gut. If she wanted to go out with you, she already would have.

The Source: Jeanne Phillips, Dear Abby

The Dilemma: "My husband, 'Roger' — sixty-four and retired — has a crush on a twenty-five-year-old woman who lives in our small community and who runs a dress shop I frequent. Roger is usually quiet and reserved, but when he sees 'Patti,' he utters loud cries and runs to her side. He examines every detail of her clothing, makeup, etc., and takes her hand and compliments her on her soft skin, her ring or the color of her nail polish. From the expression on her face and the looks she exchanges with the other women in the shop, it's clear she considers him a pest. I have spoken up and said, 'Patti must have a grandfather your age,' or, 'There's no fool like an old fool,' but Roger ignores it…What can I do to stop this?"

The Advice: "Roger's 'crush' is a reflection on him, not you, so keep your cool and please stop calling him an old fool. It's insulting and belittling, so of course he'll tune you out. Try this instead, 'Roger, when you act the way you do when you're around Patti, it's embarrassing to me. That's why I prefer you no longer accompany me when I go there.' Then, when you shop for clothing, go without him. And instruct Patti and the saleswomen that if Roger drops by without you to tell him he's welcome — IF he's buying something for you. That way, instead of a problem, you'll have a windfall, and so will they. You can even leave a 'wish list' with Patti in advance."

The Rebuttal: The first part of the advice is dead on, but the second part? I don't know what's worse — asking shopkeepers to play watchdog for you, or recruiting the uncomfortable object of your husband's affections as your own personal shopper. Tell Roger he better behave himself — and exactly what that entails — or he can't have the very-dubious privilege of dress shopping.

Photography: Inatsuka
Hair & Makeup: Nevio Ragazzini