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How Do I Show Dating-App Cougars I’m a Worthy Young Stud?

And all your other most pressing questions for adult film legend Tasha Reign

Every day, porn star and University of Southern California journalism grad student Tasha Reign wakes up to a curious string of emails from her fans, a devoted group of men and women she lovingly refers to as “Reigndeer.” Said Reigndeer ask her questions — so many questions — about her perspectives on sex, love, relationships and life itself, and as someone who’s had more firsthand experience in these areas than four adult women combined, she’s become uniquely up to the task of answering them. Once a week then, Tasha will select a few of these questions and grace us with her insight, advice and expert wisdom in the hopes that she can help you fuck and love long, too. 

I’m a 25-year-old guy who is really, really attracted to older women. But there aren’t many of them on dating apps. How, then, would you go about finding one? And do you have any tips for impressing them or showing them I’m worthy? I’m not picky so I’m open to hookups and dating.
Personally, I love age differences. When I’m the 30-year-old and my boyfriend is a couple of years younger, it’s pretty thrilling. I’ve also dated much older men. Like, much older — 50-year-old men, 60-year-old men, old, old men! And for good reason — older people are usually attractive, funny, decisive, smart, financially stable and more mature. Sure, their dicks aren’t as hard, there’s absolutely no way they’re staying up with you and they’re losing their hair, but does any of that matter? No! Older people are hot. 

That’s why I’m so glad you’re into cougars. Not only does this give you way more sex and dating options than the average guy, but you also get to help them feel fresh and sexy, something society doesn’t always do. I’m only 30, and the age-obsessed L.A. culture I live in makes me feel like I’m 45. In the porn world, I’m 60. But, my 28-year-old boyfriend definitely makes me feel young. I love it. 

You’re right, though — finding older women isn’t always easy. Mainstream dating apps are lacking in the older women department, and while there are definitely a few on there — especially on Seeking Arrangement — I think the ever-changing demands of technology scares off most of them (that, or they grew up meeting dates IRL and prefer that to swiping). That said, there are some cougar-specific dating apps and sites you might want to check out like Cougar D and CougarLife. There are even local meet-up groups in some cities where older ladies can meet impressionable young “cubs” like yourself. 

There are also a ton of restaurants and bars that have cougar nights. These are where older women go to meet younger men in person, and they’re a hell of a good time. Look up where they are in your city (if you’re anywhere in SoCal, Mastro’s in Newport Beach has an awesome cougar night).

As for how you can make an impression? Just be yourself, because that playful energy is what older women who are interested in younger men are attracted to. Make sure you compliment them and make them feel beautiful, too. I’d also recommend you let them take initiative (older women really know what they want), but flirt with them when the timing is right. Play into the young kinky thing a little bit, but don’t bring up how much younger you are too much as that can be a real turn-off. 

At the same time, be very upfront with your intentions. I once dated a 22-year-old when I was 27 (not that big of a difference, but still). It was so much fun because he wanted to fuck all the time, he lasted forever and he could get it up over and over again, but the downside was that he didn’t want a commitment and I did. So, most importantly, like any other relationship, be clear with what you’re looking for.

The guy I’m dating is a really good storyteller, but he’s always bringing up his exes in his stories. It’s pissed me off, but he tells me that he can’t help that “he dated people before me.” His favorite thing to say is, “That was 10 years ago!” Should I get over it, or should he stop name-dropping these women?
He should absolutely stop name-dropping these women. Exes are in the past for a reason and stories are great, but why get so personal and why always bring them up? Even after you expressed to him that it bothered you, he still persists? Not okay. This is bad behavior that needs to be dealt with. 

Personally, I know that bringing up exes to my current boyfriend really pisses him off. In no way does he want to hear about some guy I used to have feelings for, especially if that person is still trying to connect with me “as a friend.” So I’ve learned to not bring up my exes unless I have to. If it’s a vital part of the story or I need to talk to him about someone from my past, fine. But if I were to just casually name-drop everyone I’ve dated over and over for no other reason than to add some minor detail to a story for someone else’s entertainment? Nope. Bye. 

It’s common courtesy to take note of what your partner is and isn’t okay with. It sounds to me like you need to have a sit down with this man and set some boundaries. I know that can be uncomfortable, but you don’t want this to keep triggering you. Gas-lighting you by saying it was 10 years ago is even more annoying, so he can either respect your feelings about this or he can get gone. It’s just rude. 

Once, I dated a man that thought it was okay to bring his female friends with us to social events. Normally, I’d be happy to have them along, but with this particular guy, I realized immediately that his “friends” were just women who had feelings for him. When I addressed the issue, he’d do the same thing your guy’s doing to you: He’d tell me they were “Just his friends!” and make it seem like I was the one doing something wrong, not him. What a bunch of bullshit. 

Sometimes people really don’t know your limitations and need to be educated about them. Other times people are just stuck in their own ways, and you need to go forward without them.

I’m a guy, and until recently, I thought I was straight. But a few days ago, I had this electrifying and tense moment of eye contact with a male friend of mine, who is also straight. It sent shivers down my spine and left me kind of speechless. Now, whenever I see him, I get nervous and giddy. I’m not sure what to make of this, and it’s making me rethink a lot of things about myself. What should I do?
I’ve been in your situation before. I once had a bestie that was the sexiest woman ever. Like, I’m talking smoke show. Just soooo fierce. Needless to say, I started having secret feelings for her. 

We often did scenes together and developed a strange co-dependent relationship. It was unhealthy, and her cocaine habit didn’t help. I’d often grow jealous of her and her significant others. It bred resentment, and to this day, I feel badly about the way things ended: a screaming match in an upscale Mexican restaurant where I stormed out and even stole back her birthday present. Me not speaking up about my feelings worsened the situation, and now we don’t even talk. 

So, having been through this before, here’s my advice: Stop, give it some time and see if you still feel the same way in a couple days or weeks. You might find that your nerves and giddiness calm down a bit and that the incident wasn’t as big of a deal as it feels now. But, if your feelings get stronger or things evolve between you during that time, then fuck it! Bring it up. It’s risky because you might damage the friendship, but as proven by me, keeping your feelings inside until they explode doesn’t help. 

Maybe start the conversation by tip-toeing into the topic of bisexuality so you can get a sense of where your friend stands on same-sex attraction. Bisexuality is so much more common than we like to think, and I’ve always felt that if we hadn’t been so socialized and brainwashed by the media to think we should only be attracted to one gender, we’d fuck whoever made us feel the way your friend makes you feel. I’m not saying this makes you bisexual (or gay, or anything else), but it might be worth testing those waters with your friend. 

On that note, don’t worry too much about what this means for your sexuality. If you want this experience to open the door to you coming out as gay, bi or something else, great! But if you don’t feel like this little nervous buzz you get around your friend changes anything for you, that’s great, too. You can be a straight dude and get a little boner for a guy every now and then. It only means as much as you want it to. 

Feel free to send me your sex, love and relationship questions at tashareign1@gmail.com!