When Is It Okay To Ask A Guy To Define the Relationship? Ask A Pro

Dear Head Pro,

I am a 20-year old who has only had sex, like, once (bad experience the first time). I’m not prude, but I’m not down with having sex with someone I barely know for the first few times when it’s going to hurt and probably be awkward.

I’ve recently started talking/hanging out with this kid and regardless or not of things working out, I am comfortable enough around him to have sex with him. I’m pretty sure he does not know that I’m this inexperienced… do I tell him? If so, how? Do guys think this lack of experience is weird, especially as a sophomore in college?

What’s your best advice on how to go about this?


Not trying to be a 40-year-old virgin

Dear Virgin,

I don’t think you need to say or do anything. It’s not like it’s really any of his business, after all. If it were your very, very first time seeing a penis approach the pod bay doors I suppose you might want to tell him, but that’s still a courtesy and not an obligation. This isn’t a job interview; you needn’t fudge your experience in order to be selected. You have all the criteria you need to be an all-star sex partner: Willingness and an unoccupied orifice.

Besides not being any of his business, NO ONE wants to have to think about the person they’re about to fuck doing sex with someone else, regardless of how often or seldom it took place. You know it’s happened, but to actively dwell on it for any reason is just unseemly, you know? It’s best to keep to the task at hand, which is the two of you. Don’t stress over your “performance” or lack of experience. The best sex ultimately happens on a couple-by-couple basis, so there’s always a learning curve, so to speak. When in doubt, just do what feels good to you – it’s all the same to him, anyway. The only way for a girl to be “bad” at sex is to appear actively disinterested in the proceedings, in which case you probably shouldn’t be sexing that particular guy in the first place. You’ll be fine.

It’s only weird if you make it weird,

Head Pro

‎Dear Head Pro

So after kissing a few frogs to find my prince, as my step-dad would say, I’ve found the perfect pro: totally hot, AMAZING in bed, successful, has a great family, I’ve known his brother for about 10 years, all around has his shit together. 4 year age difference but totally what I need.

He’s everything I could ask for. I’m a one-guy-at-a-time girl, because I’ve been through the phases of booty calls, college fuck-buddies, etc. And now I just want a real potential to be with. I assume he’s not seeing anyone else because we spend all of our free time together basically, or maybe I’m naive. I’ve met a ton of his friends, he comes to my friends’ parties when I invite him, etc. My friends agree he’s older and done with his player-days if they ever existed.

Long story short is, we’re title-less. And that’s fine, for now. I’ve been asked on dates by other guys and I’ve declined just because if I knew he went on another date I’d be crushed. ‎But popular opinion is that if I ask him our status, he’ll run. Do you think that’s true? What’s stopping me from feeling empowered and asking him myself? Do you think it’s ok for me to ask if this is legit or do I have to wait for him to lay down the law?


Holding all the balls

Dear Ball Holder,

Well, popular opinion is popular because it’s easy, not because it’s necessarily correct. What “popular opinion” is describing something completely unreasonable, something that never happens. Say, for instance, you meet a guy on an internet forum where you share ideas for throwing birthday parties for cats. If you, upon meeting your cyberbuddy IRL for the first time, immediately inquire as to the nature of your relationship, then yeah. That guy’s gonna pick up his cat-sized sombreros and noise makers and run. But you? You spend all your free time together and know his family – fuck yes you can broach the subject of “what are we?” You don’t have to, like, abduct his family and bring it up in a ransom note, but there’s nothing wrong with asking the question.

Situations like these always baffle me – “well I want to do/say xyz, but I’m afraid it will scare him away.” And, ok, I kind of get that. Maybe a mostly good thing is better than no thing at all, and maybe what you want to bring up is admittedly weird, like all of your flatware is made of recycled human toenail clippings. Fine. But this, something basic like defining what sounds like a stable relationship? If you’re afraid broaching such a simple subject will scare him off, then that’s exactly what you should do. If a grown man is so terrified of such a fundamental concept, then you’re probably better off finding that out sooner rather than later.

So yes, bring it up. It can be a positive thing, where you just say you really like being with him and have been thinking lately of what to call this. He’ll probably be relieved – the language surrounding non-engagement DTR talk is awkward for adult men (saying “can I call you my girlfriend?” when you’re 25 sounds really childish). He could also disappear in a *poof* with just his hat and jacket suspended in mid-air like a fucking cartoon, but I doubt it. Either way, you’re better off bringing it up on your terms in a way that makes sense for you than needlessly sitting in purgatory.

It’s only empowering if doing it makes you feel empowered,

Head Pro


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