This story appears in the July/August 2017 issue of Playboy. Subscribe

Q:I hate dating dog owners. I love animals, but getting close to a woman with a dog seems impossible. Hear me out: The animal always comes first. Where and for how long we go on a date depends on when her pet needs to be walked, played with or fed. She can’t sleep at my place because she has to “take care of the dog.” I’ve recently been hooking up with a woman I really like, and she’s hinted at getting serious. I would…but she has a dog. Do I tell her the truth and risk sounding like an asshole by demanding to be number one in her life?—C.D., Key West, Florida

A:Let’s start by agreeing that this isn’t a “female-dog-owner” issue. All pet owners, male or female, are bonkers. Have you ever seen a man whose dog has just died? I’ve seen one cry harder over the loss of his dog than over his own mother’s death. Not just cry—weep. Men are just as conscientious as women about tending to their canines. Now, back to your question: Yes, pets always come first, and they should. They’re helpless creatures that depend on their owners to stay alive. I would know. I have a boxer. Does it suck sometimes? Yes. My dog has interrupted me three times since I started writing this. Does it impinge on my freedom? Absolutely. But that’s what I signed up for when I got a dog, and that’s what you sign up for when you date a woman who has one. Asking a pet owner to care less about his or her dog is like asking a single parent to pay less attention to his or her kid. So no, I wouldn’t risk “sounding like an asshole by demanding to be number one,” because that’s the moment she’ll realize…you’re an asshole. If you truly care about her, start bonding with the dog ASAP. Invite her and the dog to spend a night at your place. Buy a dog bed. It’s her best friend, and getting on that animal’s good side will be the key to her heart. Honestly, I don’t trust guys who don’t like dogs. Being a pet owner is a huge responsibility, and you should respect her for taking it on while still making time for you. Otherwise, start looking for a cat lover.

I live in a small city and have been single for years. Whenever I go on dating apps, I come across the same people—some of whom I’ve already dated—over and over again. Swiping through pictures and having inane text interactions with strangers always leaves me feeling empty. I know I’m ready for a relationship, but I worry that the willingness and excitement in my messages rub women the wrong way. What can I do to make sure I don’t come off as too eager?—C.A., Davenport, Iowa 
Trust me, I live in a big city and even I feel this way. When you’re single long enough, every city becomes small. I get it. But remember, you spent a lot of years enjoying your bachelor life, and there was a time when those “inane text interactions” made you feel alive instead of dead inside. Just because you’re ready to settle down with an adorable wife and get your breed on doesn’t mean it’s going to happen immediately. Don’t get jaded. Don’t get anxious. Desperation is never a good look, and humans can smell needy pheromones a million miles away. People tend to make bad decisions in a state of panic to the point that they’re much more inclined to settle for someone less than they deserve. Thirsty is the last thing you want to present yourself as when you match with a woman you like. So be honest about what you want, and no matter how much rejection, flakiness or vanity you face, remain confident that the right woman is out there looking for something meaningful too. Theoretically, all it takes is once. My tip? Behave exactly the way you behaved when you didn’t want a relationship. It’s a law of nature that the minute you let go, that thing you’ve wanted so badly will come to you. I guarantee that once you embrace single life again, “the one” will show up where you least expect her to.

I can’t come when I have a condom on, which obviously makes safe sex awkward with women I don’t know well. Any tips on how I should explain this? I assume asking her to go bareback isn’t an option, right?—P.S., West Hollywood, California
A: The first sign of an amateur in bed is someone who resists safe sex. I’m a stickler about it; I make zero exceptions when it comes to using condoms. Honestly, it trips a warning signal when a man can’t come with a condom on, because either (a) he’s not an experienced lover, (b) he’s married or © he never practices safe sex. I know I’m with an accomplished lover when he rolls up with his own rubbers. There are no protests and no questions asked. Maybe you’ve been in a long-term relationship for most of your sexual history and are just now single again. If so, allow me: Condoms are an irritating but mandatory aspect of single life, and the sooner you get used to them, the better. Some tricks: Use the thinnest ones you can find (we recommend Kimono MicroThin and Trojan Supra BareSkin in A His-and-Her Guide to Modern Condoms, March/April), and put a couple drops of water-safe lube on both the inside and the outside of the condom. A lot of this is psychological. Men tell themselves, “I can’t stay hard when I put a condom on.” Get over it. Practice putting one on and keeping it on while you masturbate at home. Sure, safe sex can be “awkward,” but once you get past that amateur view, you’ll realize not only is it for the best, it can also be part of foreplay. And no, asking her to “go bareback” is not an option. Also not an option: asking her to suck your dick instead. If she offers, well, that’s on her, but you’re not entitled to an orgasm, and she isn’t required to give you one.

I’m 31 years old. Should I feel ready to settle down and have children? I don’t.—L.B., Chicago, Illinois
Haven’t you heard? Forty-one is the new 31. Look, everyone comes of age at different times. You shouldn’t feel anything other than what you’re feeling. You can’t force something as important as being ready to take on the massive financial and emotional responsibilities that come with marriage and children. By the way, this path isn’t for everyone. And how can you truly prepare for eternal monogamy and kids? You can’t. Most people in successful long-term relationships tell me they recommit to the relationship one day at a time. Also, life hands us curveballs. Sometimes, being ready isn’t about what you can live with; it’s what—or whom—you can’t live without. And upon realizing that, voila!—ready or not, you’re ready. 

My girlfriend and I have had many threesomes with other women, but now she wants to have a threesome with another man and me. Should I participate even though the idea of her with another man—and the idea of another penis so close to mine—turns me off?—S.S., Grand Island, Nebraska
There’s often a disconnect between what turns you on in a fantasy and what turns you on in real life, and your brain and your dick aren’t always in agreement. In fact, research has found that in response to watching MMF pornography (for the newbies, that’s one woman with two or more guys), men ejaculate more sperm, ejaculate with more force and get a second erection sooner. Chalk it up to what evolutionary biologists term “sperm competition.” So don’t knock it till you’ve tried it. 

I also think it’s only fair. Unless you expressly said “I will never entertain the idea of another dick in this equation” at the start of your threesome journey, you owe it to her to open your mind and give it a shot at least once. If you hate every minute, you never have to do it again. But you may find your dick loves watching her get fucked, you naughty cuck, you. 

I don’t like my girlfriend’s friends. I’d rather do my taxes than go to her friend’s barbecue, where I’ll be forced to engage in basic small talk. Is our relationship doomed, or is there a way I can do my own thing?—J.E., Reno, Nevada
It’s important to carve out personal time, but relationships are about compromise, which, from the sound of it, you suck at. If that’s the case, all your relationships are doomed—not just this one. Everyone must engage in small talk on some level. But that’s a separate issue. More important, your girlfriend’s friends are a strong indicator of the kind of person she is. You need to ask yourself if the company she keeps is a deal breaker for you. If so, get out, because it’s only gonna get worse.


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