Sexts and Subtext with Head Pro


So this kid was at my house buying weed from my roommate (both boys) and I fell in love. We had never met but we know who each other are. I live with four other boys, two fifth years. They are all in the same fraternity (it's at Georgetown so it's a co-ed one). I didn't go to Georgetown, but I spent every weekend there and know all my friends friends. So I got his number and the following is what happened. Does he love me?


[Redacted in her best interest]

ps- you can keep the name, and the 6th image is a joke because my friend (who is my year but in the fraternity with him) invited him to brunch with us the next day
pps- i'm drunk for all of these, like day drinking white girl wasted

Dear [Redacted in her best interest],

Wow, what a prize you must be! A Georgetown townie (my favorite part of living in DC) who asks guys they hardly know for sex with the subtlety of a closeted gay senator in an airport bathroom. Tell me, does your bedroom door have a glory hole installed? You might want to look into that, just to cut out that pesky middle man known as “flirting”.  Look, it’s true that guys appreciate a girl they can bring around their buddies who won’t fuck up the mood by being too prissy or bitching about the available alcohol options. It’s also true that we appreciate it when girls (especially ones we don’t know that well) act like, I don’t know, girls. I’ve seen enough pornography in my lifetime to probably automatically qualify as a sex offender in some jurisdictions, and I still cringe when I see the euphemism for male ejaculate spelled “cum”. It’s just gross, and for a girl to use it it’s a really, really big fucking turnoff.

So does he “love you”? That’s a clown question, betch.  He hardly knows who you are (at least that’s how I interpreted “who the fuck is this?”) and you’re making it so obvious you want to fuck that people who don’t even speak English could see those texts and be offended. When you come on that strong and take away our ability to play the game, it’s off-putting and we don’t know what to do. Pump the brakes a little next time you want to bang one of your super-senior drug dealer roommate’s “customers”.

Also, I don’t even know what a “co-ed fraternity” is so I left that the fuck alone.

Keep it classy,

Head Pro



Dear Head Pro,

So I started “talking” to this guy a couple months ago. We went to a lot of each others’ date functions and call me a tease or whatever, but we never really went much past making out. Fast forward to Cinco de Drinko, where somehow after a few too many tequila shots I blacked out and apparently forgot to mention the minor detail that was my virginity to him before we had sex. I have no recollection of the night, but I guess he had an inkling and kindly reminded me of said event a week later. My heart dropped. I tried to play it cool, but I had always planned on losing my virginity to someone I was in love with in some sort of romantic setting; instead I lost it to a frat guy in a sombrero. I had a minor freak out (see attached paragraph) and attempted to set the record straight by letting this bro know that he should not be expecting sex the next time I came into town. I expected that this guy would’ve run away as fast as humanly possible, never to be heard from again. Instead, he’s been texting me every day. I do have feelings for this guy, and I’m pretty sure he likes me too. I would like to be on the relationship track when I get back into town in the fall, but I am obviously clueless in how to keep this guy interested now that I’ve already given the milk away for free. So my first question is, what’s the best way to let this dude know that he is the proud owner of my v card? Second is, how can I regain control and get on the relationship path?

I’m Not That Innocent (Anymore)


Dear I’m Not That Innocent (Anymore),

Yeesh, sorry things turned out that way. I want to know though, was he just wearing the sombrero throughout the day, or during sex too? It’d be a lot cooler if he was. So, the bad news is you lost your v-card in a way that failed to meet your expectations. You know who else that happened to? Every fucking girl on the planet who’s had sex. Sure, sex is the best thing ever besides Chick Fil A sandwiches and boat shoes, but it’s often less a romantic, magical act and more an athletic endeavor involving bodily fluids and cramped muscles. So yes, you’re bummed you don’t remember your first time. That’s understandable, but in reality you might be better off because it probably wasn’t pretty, and wouldn’t be regardless of the circumstances. The good news? No one fucking cares. Sex doesn’t have to be for the first time for it to be good, and in fact the more you do it the better it gets. If it sucks, you can always try again or find someone else.

Regarding your actual questions:

1) Wait as long as you can, preferably until you’re in a stable relationship with him. If that doesn’t happen, then he never fucking needs to know. Telling him now might freak him out, and the explanation you gave him was more than sufficient.

2) What I get from his texts is that a) he seems like a decent guy who does appear to like you and b) based on his last text, he doesn’t believe for a minute that he’s not taking you for a ride on the bonercycle when you come back. I don’t blame him for having the expectation, and I don’t blame you for having your reservations. I think you gave him a decent explanation and made your feelings pretty clear, so all you can do is see what happens.

I don’t think you need to worry about this being a hit and run. It doesn’t seem as though he “counts” the first time and may even feel a little bad about it since you were so shitfaced. See how he proceeds once you get back, and remember that you can’t get your virginity back. If you’re holding out, make sure it’s because of your gut feeling and not some moral stance you’re futilely trying to uphold. It’s like George W. said: If it feels good, have sex with him.

Tequila Kisses,

Head Pro


Last weeks Sexts and Subtext

When you're texting with guys (or your frenemies), do you ever rack your brain over the difference between “hey” and “what's up”? Is he trying to play it cool, or is he just not that into me? Does using emoticons make him gay (hint: yes)? Head Pro is here to help.

Take a screenshot of your text convo and send it with your burning questions to . He'll interpret the s(ext) conversation, tell you what he thinks is REALLY going on, and out you for probably sounding desperate and clingy.

Please include a little context, and get ready for some sextual healing.

PS. If your phone's too fucking old to take screenshots, you need more help than we can provide.

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