Miss Information

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I'm twenty-nine-years old. How can I lose my virginity?

by Cait Robinson

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Dear Miss Info,

My guy and I have known each other for three and a half years and been dating for two years, long-distance — he lives on another continent. We love each other a ton and get along great, but we've only ever been physically in the same place for two weeks at a time, every few months. I'm now graduating from grad school; he'll still be in school over there for another year. The hope is for him to eventually get transferred over here, through his job. So my question is whether or not I should move there right now.

On the one hand, I feel like this is the time for me to really start my career here, especially since this is where I want to live long-term. Moving there would mean putting things on hold for at least a year and possibly letting my skills deteriorate — I wouldn't be able to get much work in my field over there. And it's risky to put my career on hold to go be with someone who I've only been with for such short periods of time. On the other hand, I don't know if we can survive another year being long-distance without knowing when we're going to be together for sure, and I'm the one who is free to move right now. He wants me to be able to pursue my career, but he is also miserable being apart. Should I seize the opportunity now and move there for a year to see if we're actually good together? Or should I work on my career now and hope that if we really want to be together, we'll make it through another year?

— Skill Set Half-Life

Dear SSHL,

All right: on our left, we have "miserable, with a paycheck," and on our right we have "taking Valiums and baking pies to kill time." Pick the pies! Pick the pies!

I'm sort of joking. In all seriousness, there's a ton of really meaty middle-ground here. If you're willing to put yourself in potentially uncomfortable situations (i.e. move to another continent to give a relationship a shot), you can have your Valium pies and eat them too. Let's say you decide to move there. I say go for it — with the following provisos:

• Career development doesn't need to be a linear thing. You don't say what your industry is, but even if you can't find a job in your field, you can absolutely acquire skills that will pay off later. If you're a writer/editor, take a web-design class; if you're a biologist, get a job at a botanical garden. Study a foreign language regardless. Broaden the lens of what might make you employable. You may lose steam in some areas, but a year abroad, if done correctly, can bolster your employability, not sink it.

• Have an exit strategy. This means do not sign a lease. Do not get drunk and "ironically" marry your boyfriend. Even if you decide to live together, make sure you have enough money to fly home if things (somehow) get bad. Sure, it may sound paranoid, but it's better to have $2,000 untouchable in your bank account than to be stranded.

• Be prepared to make your own community. The biggest bummer of being abroad, much less moving abroad for a significant other, is feeling like a friendless loser. Pre-game your trip by researching book clubs, meet-ups, Dungeons and Dragons leagues — anything that allows you a life outside of your boyfriend.

• And, of course, talk it out. Predictable, I know! Make sure both you and he know what you're getting into, in realistic terms. Make sure you're both clear on trajectory: if you make X sacrifice and expect him to make Y concession in the future, talk it out now before it happens.

Ultimately, one year of your life won't make or break your career, as long as you remain active and engaged with that year. Make sure you're excited about whatever plans you make, rather than feeling like you're settling. As long as you don't disappear into a haze of affection and baking, whatever you decide should work out fine.

Dear Miss Information,

I'm a twenty-nine-year-old woman. I'm a virgin and I've never really been kissed. Most people out there have given me endless tips on finding "The One." But I don't want to get married. I just want to get laid!

I have little to no sexual experience beyond a couple of frat-party dance-floor makeouts and one drunken high-school blowjob. I've never had a sexual experience with a man in bed. Vibrators and internet porn have been very good friends of mine. I dropped out of college when I was twenty and any and all momentum I had going stopped. I stayed in the same town and my self-esteem took a blow. There wasn't much traffic leading up to that, but at least there was a consistent pace. I admit I'm insecure and see that I have control issues, but I do meet single men and recently joined dating sites. I am a student again and have always been good at casual flirting.

But I get the same old advice: dress cute! Be confident! Make the first move! Okay, okay, okay, I get it. I make my own fate. But, seriously, I can't take it much longer! That strategy seems reasonable because people assume I'm just trying to get myself married. I mean, I'm twenty-nine —why would I be asking for tips on how to pop my cherry?

I've never had a man really want to kiss me, touch me, fuck me, and let me kiss, touch, fuck him. It would be ideal for an aggressive, direct man to appear and help me out, but that wish is just another delay tactic. It seems to me that getting a little action would validate me — for myself — as a person men want to sleep with. Should I just continue to dress cute and flirt and send emails on dating sites, hoping that one coffee date will lead to another and then eventually a tender evening under the sheets? Or should I head for the bars? Propose a little experimenting with someone I already know? Take out an ad on Craigslist?

Counseling for emotional baggage: done. Online-dating profile: done. Cleavage and lipstick: done. But what should I do now?

— Betty Boop

Dear Betty Boop,

It sounds like you've got a good grasp on this issue, and you've even got a solid dose of humor about yourself. Gold stars on gold stars. So here's my question for you: are you enjoying any of this? If you're not, jettison it. Push-up bra digging into your ribs? Give it to Goodwill. Lipstick drying out your lips? Trash can. Find the internal compass buried underneath the advice chatter, and go with that. Ultimately, you can pick up men anywhere. If the bar scene feels like a slog, or a bass-thumping means to an end, don't waste your time there. Hang out where you want to hang out, and talk to people you want to talk to (regardless of whether or not you also want to bang them). That authenticity will take you farther than tequila shots.

Now, let's come back to this "low self-esteem" business. Self-esteem is not necessary for getting laid, but it is necessary for attracting the kind of people you want to get laid with. Take this line: "A little action would validate me… as a person men want to sleep with." I get the validation issues, for sure, but "I'm not worth sleeping with" is the kind of message that seeps from your pores, meaning even interested guys might sense it and turn away. You also say you've never had a guy want to be with you, which seems like an issue of perception (i.e. how you remember the event) rather than reality. You're in counseling to work on the self-esteem, which is great; now set your sights higher. You deserve an honest connection.

Because you asked, here's the secret to getting a guy to do you, courtesy of my friend Sam, who was reading over my shoulder: "Stick your tongue down his throat and say, 'Want to come back to my place?'" (Sam is a national treasure.) Let me add some nuance to his point. Getting any guy into bed isn't really the hard part. Getting what you need from the interaction is. Actual validation — the lasting, worthwhile kind — comes from respect, not just attention. Shift your search away from "warm-blooded male," and start looking for "a guy who respects me and wants to do me." Everybody deserves to have someone around whom they feel safe and comfortable. Setting these standards does not mean you're seeking marriage; it means you think well of yourself. That's the kind of message you want to telegraph.

Is Sam's recommendation not working for you? Try Nerve Dating instead.