Ah, the Shy Guy: that rare specimen of man who you’ll never overhear  talking bragging about some meaningless hook-up. You won’t find him at parties or see him hamming it up for the ladies. He’s sweet, modest and avoids being the center of attention at ALL costs. Odds are, he’ll be the one sitting in the back of class, avoiding eye contact with the professor when he or she scans the room for a volunteer.

He’s pretty much adorable, really. Mysterious, intriguing, sensitive, endearing … a diamond in the rough (“the rough” being the obnoxious, masochistic guys that are just way too common in college). Shy guys are hot. Think Michael Cera. Mmmm.

No? Just me?

Anyhoodle. You’ve caught him glancing furtively in your direction on many (many) occasions. You’re interested. He’s interested. But the two of you both know there aren’t gonna be any suave, hey-baby-what’s-your-sign moves on his part. So, short of holding up a “Hey. You’re cute. I’d say yes if you asked me out” sign, how d’ya go about meeting/cracking open the shy guy?

Approach him casually and strike up a small convo. While he prrrobably won’t be bowling you over with witty banter and charm, he won’t run away. Do most of the talking, but toss in lots of open-ended questions. Just keep it light and impersonal at first: topics like homework, professors, something on the news. Do this a few times a week to establish a bond and tear down that wall he’s got up.

Spend time as friends, without pressuring him about dating. Hang out with him alone, rather than with your other friends. Be patient. It takes the shy guy some time to become relaxed and show his true self.

Be approachably attractive. The root of shyness is insecurity, so it’s more than likely that he thinks you’re out of his league. So now isn’t the time to try out cutting edge fashion or over-the-top makeup. Try for “cute” rather than intimidatingly gorgeous (that’s a toughie, I know).

Arrange a few quiet dates if he doesn’t get up the nerve to ask you out. Keep it casual, and— again — keep it one-on-one. Clearly, the shy-guy isn’t going to do well in a large group of your girlfriends shrieking about vibrators. Choose something low key and easy like a movie, where there’s less pressure to talk.

Gauge his feelings for you. Talk about what you’re both looking for in a person, and drop hints that what you’re looking for is him.

Help him feel confident around you. Every male has an ego — find ways to boost it sincerely. Subtly compliment him. Let him help you with something, whether it’s a homework problem, fixing your computer, or finding the latest gadget. Or — and this is probably the best confidence booster–  see him when he’s in his element. He’ll be MUCH more open and charismatic when he’s somewhere he feels totally comfortable.

Once you enter the relationship zone: First of all, yay. Second of all, introduce him to your friends and family slooowly, starting with the quiet, less intimidating ones. Yeah, save loud Uncle Frank and Over-The-Top Tina for when he’s more comfortable in the relationship.

The shy guy is SO worth the effort and patience. Think of him as … a gift. A treasure to unwrap. A rare and special treat that not everyone gets to see. If you can stick out a few awkward silences in the beginning, I guarantee you’ll have landed yourself a respectful, fun and totally caring guy.

[Photo courtesy of MariaTarescaCB on Flickr.]

Nina Hartley is an extremely successful adult film star with 650 different video appearances under her belt. Starting off as an exotic dancer in the ‘80s, she is now a published author and an award winning actress for both sexual and non-sexual roles. I met Nina when we both served on a panel about modern sexuality for the Commonwealth Club in San Francisco. I asked her to give me some of her wise wisdom about sex, relationships, and everything in between.

Me: Do you think sexual freedom (through porn, sex outside of relationships, etc.) is good for the advancement women, or detrimental to the advancement of their self esteem?

Nina: Sexual freedom and autonomy are vital components of women’s greater equality in society. We are adults, not children in need of protection. Whether or not a woman’s exercise of this freedom is good or bad for her depends upon her making choices that are consistent with her values and beliefs. When we do things that go against our understanding of ourselves and the world, bad things usually happen as a result. My choices wouldn’t be good ones for very many women, nor would their choices be good for me.

M: We all know the key to being sexy is confidence. Do you have any special advice for being, or even just appearing, confident? Perhaps something you picked up through the industry?

N: Confidence arises out of our being centered in ourselves, which comes from knowing and accepting ourselves as we are, not as we think we should be, or how or parents have told us to be, or what we think society says we must be. The most important thing I learned from dancing (my earliest adult career) was that no one can read your mind. So, head up, shoulders back and smile. Your inner confusion or insecurity will pass unnoticed by those who, having just met you, only see what you present to the public. Speak directly and clearly, without apology, about what you want and don’t want.

M: Many women have trouble having sex with someone without becoming emotionally attached. From your experience, is there any way to separate sex and emotion? Or does that just come with practice and time?

N: It’s hard, though necessary, to separate how we, as individuals, actually feel about the sex/emotion connection … Some women (and men) cannot make such a separation, and they need to be that much more stringent about how, when, why and with whom, they choose to become intimate. Each person’s obligated to his or her own safety, security and comfort. Part of growing up is learning how to resist pressure from those who would have us cross our own boundaries, which we usually do by having x number of unpleasant experiences. It’s only possible to separate sex from emotion if one is “built” that way, as I am, or by suppressing his or her true feelings with drugs, alcohol or denial, which is never good. With experience, most people find the way that is best for them.

M: Do you have any last words of encouragement or advice for college-age women?

N: Know that it’s normal to be insecure about sex at your age. You’re young adults and have the obligation to differentiate yourselves from your families: what values about sex do I share with my family/parents and want to maintain? What values of theirs don’t work for me? How can I both experiment with sex AND keep myself safe, both physically and emotionally? Educate yourselves about safer sex and birth control. Get a dose of the morning after pill when you don’t need it, just in case you find that you do. DON’T USE ALCOHOL OR DRUGS TO SUPPRESS LONELINESS AND INSECURITY. It’s okay to say “yes” to sexual activity that fits within your boundaries for same. It’s okay to say “no” to sexual activity that doesn’t fit within your boundaries for same. When in doubt, slow down.

What do you think, ladies?

Is there something wrong with that?

That’s the question, isn’t it? In a world where it’s normal to partner up, get married, and have children, it often seems to me that those who fall outside the norm are harassed for it. What exactly is so wrong about wanting to be single for always? In my mind, that’s a matter of preference and a personal choice for which no one should be discriminated against.

If a person is single and wants to be in a relationship or have children, that’s one thing. But if they don’t—lay off!

Sometimes it’s parents who are the culprits. If their child doesn’t seem to want the suburban dream of a spouse and a decimal-pointed number of children, that child is looked at as an anomaly. “When are you going to get married?” the parents will drone—or, even worse, “When am I going to get some grandchildren?”

To those parents, I say, Go volunteer at a preschool, and leave your kid alone.

Just as it’s any married person’s choice who to marry and why to marry, it’s any other person’s choice and right not to do the same. Just because someone is past the glow of youth, is not married, and does not have children does not mean that person is a pedophile, a criminal, socially awkward, or desperately unhappy.

Singleness is not a problem to fix. Period.

[photo from www.nubar.com]