Dear Miss Information,

I've had sex with one man in my life and I love it. He makes me warm and happy, and sex with him always leaves a smile on my face. The sex is good, so I can't figure out why I've never had an orgasm. We've tried different positions, toys, and role-playing, but nothing hits the spot, so to speak. My boyfriend's been understanding about it, but I can tell he's starting to doubt his own ability, and it's bothering him.

I've tried to justify it to him (and quite possibly myself) by explaining that I was sexually abused when I was younger. Except for the occasional panic attack, I've gotten over the abuse since being with him. Trust is really an amazing thing! It no longer has a huge impact on my life or my sex drive. I really don't think that's the problem, though. I'm not able to orgasm from masturbation. I find that masturbation lacks the intimacy my partner brings.

Should I see a medical doctor on the chance that it's medically related, or a therapist in case it really is rooted deep in my subconscious? — Orgasm Free for Now

Dear Orgasm Free for Now,

Yes on both counts. Keep in mind that most shrinks aren't like the ones portrayed in Mad Men. They're more likely to ask you what happened to you this week than mine the depths of your subconscious. If you're looking for a big "ah-ha!" moment, you might be disappointed. They are still great sources of insight, though — as are sex therapists. Speaking of, find one in the American Association of Sexuality Educators Counselors & Therapists directory. No quacks butt-plug-wielding quacks here. All these folks are certified, vetted, and ribbed for your pleasure. 

Give yourself a big hand for all the hard work you have been doing: the role-playing, position switcharoos, and sex toys. A lot of people never get anywhere near that level of sexual openness, and they haven't had to deal with one-tenth of the trauma you have. 

I have to ask: are you absolutely sure that you're not orgasming? I know that sounds like a dumb question, but bear with me. Girls don't have that big showy ending that guys do. You may be so focused on the end goal that you miss the fun. I was orgasming for years as a teenager but didn't know it. I just knew that, after a certain point, everything would go numb and I'd have to stop. Female friends had similar experiences. It takes a while to get to know the story arc — there's a beginning, a middle, and an end.

That's why masturbating is so awesome, Orgasm Free for Now. I know it's not as "intimate," but it's not supposed to be. Sometimes we need that freedom to be selfish. To make weird faces and think whatever kinky, demented thoughts are necessary to get ourselves to that state. Have your boyfriend lie down next to you while you do it, if that makes you more comfortable. Experiment with video chat or phone sex. Trying to come through penetrative sex before you can come on your own is like going for three pointers when you don't yet know how to dribble the ball to the basket. 

On to your boyfriend's self-esteem. Continue with the verbal reassurance, but back it up with action. Don't just say you're enjoying the sex — initiate it. Come up behind him when he's doing the dishes and grab his ass. Give him a no-reciprocation-allowed blowjob. Let him enjoy himself without the worry of being a failure, yet again. Yes, you deserve to come. And you will come. When the pressure's off and the time is right. Or wrong. It's not something you can plan. Give yourself permission to stop trying so hard. A watched honeypot never boils.

Dear Miss Information,

I'm looking for advice on how to obtain a background check on a potential date. I don't want him to know, obviously. I'd like to find something free. I have never been on an internet date, as unbelievable as that sounds, and would just like to take every precaution. Thanks. — Single Mom  

Dear Single Mom, 

Have you seen Swimfan? Don't. It's terrible. As bad as Fear but without Marky Mark's abs. I just mention it because of the premise: girl meets guy. Girl stalks guy on the internet. Girl... sparing you an hour and a half of your life, I'll just remind you that online crazy comes in both male and female flavors.

Internet dating is not that different than regular dating. You can meet a nutter at church just as easily as you meet one in a chat room. The basic rules of common sense apply: trust your gut and don't reveal too much personal information.

Most dating sites discourage you from sharing personal information until after the first meeting. Some will even flag messages containing phone numbers or emails. Still, a bit of light chitchat should yield what the person does for a living, where they went to school, their last name, and/or email.

If you have a last name, this site is one of the few that pulls up criminal records without requiring a fee or registration. Be careful, though. What looks like a red flag could be something totally benign, like an unpaid parking ticket.

Email addresses allow you to conduct searches on social networks like Facebook and photo-sharing sites like Flickr. You can also do a plain old internet search using what little you do know about him: "John + Michigan State University + tax attorney," for example. All you have is his dating-site username? Try Googling it. People often use the same one across multiple places. 

Remember, there's such a thing as knowing too much. Read enough, and you'll come up with a reason not to go out with just about anybody. It's better to get to know someone in person before diving into their personal thoughts and childhood pictures. 

Plus, the more you know, the more you're going to want to discuss it, which will make you look like a psycho. It's hard not to bring up what you found while you were Googlestalking, especially if it's irresistible conversation fodder, like if your date is BFFs with Seth MacFarlane or has a bunch of bizarro stuff for sale on eBay. You can tell yourself you'll be quiet, but it gets harder after a couple of tongue-loosening cocktails. He'll assure you that "it's cool" and "he understands" but you'll never hear from him again.

There are also digital footprints you leave. Not all sites log it, but more and more are starting to list where you came from. How humiliating would it be to have him know you visited his profile seven times in the last five days? If you're smart you'll limit your snooping to what's necessary in the name of personal safety. 

Readers, are you pro or anti-Google searching before a first date? Where do you draw the line between cautious and crazy?

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