The Hook Up: Questions from a Confused Virgin


I’m in a new relationship; it’s been about a month or so. I’ve never been with anyone before (and she knows this), so everything is a new territory for me. We had several dinner dates, and somehow all of them involved intense make-out sessions afterwards. (Is this normal? Is that what dating involves?) 

I’m flattered that she’s interested in me that way, but now I’m starting to wonder if this is just a hook up. I’ve suggested that we go out and do stuff together (i.e., bowling, museums, etc.), but she declined. She says she doesn’t like crowded places or that she’s tired from work. Then, she tells me that she’s going camping with a close girl friend for a week. I’m jealous, but I don’t want to be clingy. Now, I’m afraid to have sex with her (more so than before) because I feel like she might just leave me afterwards. Am I overthinking this?—The Confused Virgin

I’m jealous, but I don’t want to be clingy. Now, I’m afraid to have sex with her (more so than before) because I feel like she might just leave me afterwards. Am I overthinking this?—The Confused Virgin

Dear CV,

Yes, you’re dating! Casually dating, but dating nonetheless. And yes, dating tends to involve activities like dinner and making out. I suspect you already know this, deep down, unless you were raised in a sex cult and/or a home in which you were not allowed to consume any television or movies ever.

My guess is that your confusion and angst is coming less from fear of breaking the STRICT DATING RULES (because there aren’t any really) and more because you don’t know where you stand with this girl.

This is understandable.

Also, I have no idea what she has against bowling or museums, because those are objectively great dates.

First thing’s first. You’re not “just a hook up.” Those tend to involve “meals” consumed purely in liquid form and not a lot of conversation. That said, if you’d rather have sex for the first time with someone who will stick around for a minute, you might want to communicate that to her.

Now, the “close friend” camping trip. If it’s upsetting to you, then by all means ask her if this gal is more than a friend. Keep the conversation casual and you won’t come off as clingy. Try to remain curious and open when you ask about it. And be prepared to get an answer you may not like.

The bigger concern, at least from my vantage point, is that you appear to be placing a lot of expectations on this one gal to show you all the dating ropes. But she might not play that role for you. She might show you one measly rope and then you’ll realize you’re not compatible. Or she’ll show you a few ropes, enough to make a nice lanyard, and then move on. Or, who knows, you might fall madly in love and shun all bowling alleys forever.

The whole point of dating, though, is to HAVE FUN! Are you having any fun? Are you enjoying learning about a new person and making out with that person? Are you dating other people? You might want to, because it’ll alleviate some pressure you are feeling. Plus, the only way to get dating experience is to go on dates.

So with that in mind, chillax a little. Focus on the here and now and ask yourself what it is you even want from this girl, and from dating in general. Do you want a serious girlfriend? Do you want to meet new people and have fun? Do you want someone to do activities and make out with while you get more comfortable with the idea of sexytimes?  

Try not to worry about whether you’re “doing it wrong”—You’re not! We are all just making it up!—and to ask yourself instead what it is you’d like from a romantic or sex partner. What would you like to get out of this experience of getting to know one particular person and can you be OK with some uncertainty? Can you look at your life as a great adventure, one you might not have all the answers to but can nevertheless find enjoyment in?

As the poet Rainer Maria Rilke once said, “Let everything happen to you: beauty and terror. Just keep going. No feeling is final.”


I’ll keep this short and sweet. I want to help my girlfriend have bigger, better orgasms. As of now, she tends to come quite easily, and her orgasms are “wimpy” (her words!), more like small tremors or waves. (Not that there’s anything wrong with that!) What can I do to better rock her world?—O My

Dear O My,

A few things: Kegel exercises and tease her like a motherfucker.

Kegel exercises, as you may know, are when you contract your PC muscles (the ones that, when you’re peeing, stop the flow of urination). If you’re not sure which muscles do that, the next time you’re on the toilet, try to stop yourself from peeing. Those are the muscles you’re targeting.

Exercising your vag means you’ll be able to contract those muscles harder during sex, leading to more intense sensations and to bigger Os. How to do it? Try working the PCs at least once a day, either with some slow, long squeezes or a few fast, short ones. There are also toys that facilitate this, but they’re not super necessary for your purposes. Make it a habit by kegeling during one of your routines—brushing your teeth, for instance, or when you’re at the office water cooler. After a few weeks (give or take), you should start to see results. I recommend you both do it together, so it doesn’t seem like you’re giving your girlfriend homework or something. Unless she’s into that. 🙂

Second, practice bringing your lady to the brink of climax, until she’s just about to come, and then back off for a bit, and start the process over again, getting her hot and heavy, but not taking her over the edge. Do this until she’s writhing and squirming and can no longer stand it. Then let her come. Generally speaking, the longer the build-up, the better the payoff.

Good luck!

Anna is a freelance writer in Oakland. Get overly personal emails and haiku from her at Or Twitter @annapulley. Send her your Hook Up questions at