Porn Star Advice: How To Date A Dad-Type

As real-life, fully-certified porn star Kayden Kross says, “You can’t faze me. After all, I’m a notably awarded citizen, and 30 million eyeballs have interacted with my butthole.” Indeed, we’ve tried. Thus, we’re proud to have her as our official sex columnist. With her huge collection of experience-backed tokens, Kayden will be lobbing her left-fielded, unsubstantiated advice straight at the level of your forehead... well... only with your consent, of course. To get your question seen (and possibly answered) e-mail Kayden@Nylon.com. Now, let the oversharing begin.

Question: I have a huge fetish for taboo role-play. I love "Daddy" types, and I love playing out the different scenarios I sometimes see in porn. It's a huge turn on—at once being submissive and giving up control and knowing that I am pleasing my "Daddy." It's important for me to say that I am not looking for "Sugar Daddy." I just love an older (between 35 to 45; I'm 24), dominant guy to be loving of me both in and out of bed.

I have a couple challenges with this fantasy. One issue is with my dating life. I usually find these dad-types on Craigslist because I don't know how to meet them in real life, and I've also never been approached in person either. Another issue is more with intimacy. I can't seem to find a "Daddy" who wants to see me as more than a one-night stand, which, in turn, has kind of traumatized and prevented me from developing a long-term relationship. And finally, my third issue (for now) is that I have this internalized fear about it being more societally appropriate to date someone closer to my age and I really would love to figure this out if it's possible to have that.  

Answer: Dear Sexually Confused 24-Year-Old, 

Let’s work backward through your question, and then hopefully we can get the kink worked out of the problem and get you on your way to having a fulfilling relationship with an older man. What I’m gathering is that you feel your attraction to an older man is perhaps too taboo, which is why you worry that you’d have to keep it hidden from your family and society, hunt in the dark back pages of Craigslist, and aren't probably sending out the signals to potential mates you might meet in your day-to-day life, and, as a result, not meeting anyone at all. I hope I’m not being too plain in saying this, but it’s just not that taboo. Older men have been dating younger women since the dawn of time. While not all older men are looking for significantly younger women, I feel that I can pretty safely say there is no shortage of older men who would be over the moon to discover someone like yourself—who is sexually excited by the fact of their age—so much so that she has combed the likes of Craigslist just to approximate the experience of having a romantic relationship with someone like them, if only for a night. There is a wealth of older fish in the sea, my dear. If you cannot find them, I wonder whether you’re purposefully not casting a line out there because of your fear of how you will be perceived.

But if you don’t believe me, then let's just look for a moment at what it actually looks like when you date an older man. Sure, I can’t speak for your family or those close to you—I have no idea how you were raised—but I can speak as someone who occasionally comes in contact with society. David Foster Wallace has this quote that I’ve always loved a little too zealously: “You will become way less concerned with what other people think of you when you realize how seldom they do.”

Society is not a brooding mass ready to always drop the guillotine when you overstep a perceived line. Society is a group of individuals mostly preoccupied with themselves (that occasionally becomes a brooding mass if you really fuck up—but dating the wrong person does not qualify, minors aside!). So if you meet a man who has a couple of decades on you, and the two of you decide to spring for a romantic dinner for two at your local Denny’s, don’t hesitate to enjoy the occasion on account of it being taboo. It’s just not, and no one cares. Eat your eggs.

If you’re worried about your family or close friends judging you, then you have every right, as an adult woman in the world, to take your time to be sure that the relationship is one you want to weather their storm over, and then tell them. But don’t apologize. They will have whatever reaction they will have, and then some time will pass, and one day you’ll wake up and this handsome older fish that you snagged will be a gloriously mundane part of your daily life. They will accept it or they won’t, and it’s no matter because they’re not the ones who have to date him. You are. And your situation now is exactly what will become of you if you are not allowed to fulfill this need. It’s not fair that a group of people who are supposed to care for you and your happiness would prefer you to continue to feel isolated and insecure just so that they can sleep better at night knowing you’re not happily cuddled up next to someone who is—god forbid—older than you.

Okay, in a perfect world, I told you not to worry about how you’re perceived and you just magically shrugged that hang-up right off, and now you’re ready to fish. Next bit of advice, which you seem to already be peripherally aware of: Stop fishing for something you're just going to throw back. If you're looking for something temporary on Craigslist, that's probably what you're going to find. No matter if the reason you think you won't find anything stable because of what society says or because of your own insecurities about looking for a daddy, if that's what you're putting out there, that's what you're going to find.

Meeting people who might become meaningful candidates for a meaningful relationship requires meaningfully putting yourself out there. It’s risky, sure. You might be turned down. And, in your case, a lot of good men who might be thrilled to even speak to you will probably naturally refrain for fear of appearing predatory by giving attention to someone much younger. So it’s on you, babe. You see a guy who is your type out a coffeehouse somewhere, it’s likely going to be your job to send the first flare. It doesn’t have to be anything overtly showy. Eye contact is often all it takes to start a conversation with someone who thinks you don’t look too shabby yourself. If you feel that the real world might be too brazen a place to cast your net, though, you wouldn’t be the first. I don’t blame you. It’s scary out there, and also requires changing out of pajamas.

But! I think you might have passed over an easy solution to this dilemma by too readily passing off “Sugar Daddies.” See, I get that you aren’t looking for money, but I’ll let you in on a secret: a lot of men aren’t in the Sugar Daddy game because they need a creative place to put their money. They’re there because they’re looking for exactly someone like yourself—who is interested in them at their age—and they think that the only way to find a relationship with a younger woman is to pay for it. They’re also looking for relationships, perhaps even meaningful ones, or you’d have stumbled across them on your local Craigslist ads instead. So, maybe try fishing in the lake that is already guaranteed to be full of the particular fish you’re after. You can let them know loud and clear that you’re not in it for the money in the headline, and that you’re looking for something meaningful, and even—if you’re feeling adventurous—go into the exact extent of this "Daddy" role-play you’re after without having to be present for any perceived rejection you might feel should anyone pass. That’s the beauty of online dating! You can put all of this out there at minimal risk, all with the guarantee that it will be seen by a perfectly suited audience. After all, if you can’t find your “Daddy” on a dating site that has the word “Daddy” in the name, where can you find him?