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Spilling about Sex and Meeting Women
The Maven gives advice on coming clean about your dating past and talking to women.
Tuesday Oct 02, 2007.     By Anna Pulley
Centerstage Chicago Nightlife City Guide Arts

Dear Maven,

I'm having a slight issue of conscience lately. I'm a 30-year-old lesbian who has been seeing a wonderful woman for about six months now. The problem is that I haven't told her a lot about my romantic past, and what I have told her has not been the complete truth. You see, I have been out as bisexual ever since I was 19, but only came out as a lesbian at 29. Before her, the only situations I'd been in with women were flings with bi-curious straight women, and I've also had two long-term relationships with men (regretfully, but still). She's someone who has been out (at least among friends) and has never so much as experimented with men. Thus, I feel strange coming clean about that part of my life to her, especially when it feels like an embarrassing subject for me. But I don't know how far our relationship can progress without honesty. Any suggestions?

Sincerely,
Bi Default

A: I was bi-bashed recently by a rather rotund gay man, who told me that bisexuals can't make up their minds. "I don't have a problem making up my mind," I told him. "For instance, I don't like you very much." So I empathize with your situation, Bi Default. It ain’t easy coming "clean" in a culture that is so sexually linear. Very few lesbians are lifers, meaning they've at one point or another sampled the male species, and some continue to partake even after they've expressed their love for the ladies: We call these people "Republican Senators." I'm curious, though, why you say your sexual past is an embarrassment? Did you date Kid Rock? You can tell me; I'm an expert. Even if you did, you should probably come clean to your girlfriend, if for no other reason than it's going to come out eventually anyway, and you won't want to be known as "that big fat liar who dated Kid Rock." (Trust me, I've been there and it is a lonely place.) Ask her a specific past relationship question and then share one of yours in return. Something like, "Ever been caught by your parents?" Or, "Have you been to a NASCAR race?" Bonus points if your story involves something lame your boyfriends did; that will reaffirm how much better she is than they were and it will endear you to her further. Anything involving incarceration, puking or lighting things on fire will work nicely.

And don't forget that oft-cited queer word, "pride." Being ashamed of your past never got anyone anywhere, except Scott Baio, and even then, it only got him a reality television show that showcases his pathetic-ness for the entire world to laugh at. You can do better, I promise.

Dear Maven,

I am 25 years old. I've never had a girlfriend. I've been on two dates, and I have only had sex twice. I guess you could say that I am in a dry-spell. I work from home, and I am generally reclusive. When I get around women, I become nervous and always say the wrong thing. In the looks department, I would say that I am average, but I see guys who look a lot worse than me getting many women. Do you have any advice for me?

Sincerely,
Anonymous

A: Getting women is no easy task. I can't even count how many bars, coffee shops and family reunions where I've been shut-down at trying to score with chicks. Luckily, I've been watching VH1's The Pick Up Artist and can now confidently offer tidbits on chatting up women AND the secret to applying smudge-free liquid eyeliner. The one thing that separates the unattractive dudes who get chicks from the mildly attractive dudes who get chicks is this: necrophilia. No wait, it's confidence. Ever heard the phrase "fake it till you make it"? That's the attitude you need to have when you approach a woman. It doesn't matter how many people you've been with. What does matter is that you appear to have confidence. How to fake it? Project your voice, make the conversation about her, be polite but assertive and, if there's a Volkswagen nearby, bench-press it a few times. Being reclusive is a minor snag, but why do you think God invented instant messenger? Partly it was so Drew Carey would stop sending Him explicit emails, but mostly it was to help shy, nice guys like you meet women from the comfort of their own homes. Starting from scratch is hard, which is part of the beauty of social networking sites; a lot of twentysomethings have online profiles or blogs that tell anyone who stumbles upon it things you probably didn't want to know about them, but that can be used as conversational fodder nonetheless. For instance, "I see from your MySpace page that you like canned corn and hittin' it from behind. I too enjoy these things. Would you care to chat sometime?" That's how I met my first husband. If it worked for him, it can work for you, too.

Anna Pulley, our Meet-Market Maven, has been on more bad dates than J. Lo's been to divorce court. She's been a one-date wonder and Wonder Woman. She's bi, and no she doesn't want to sleep with your boyfriend, thanks. When she's not giving advice, she enjoys theme parties for every and any occasion and working as a Carnal Consultant for Early to Bed. Buy her a drink or ask her a question already.