Much has been written about feeling mystified about the opposite sex. That confusion is the reason behind countless books, articles, movies—you name it. That’s to say that feeling unsure about dating is a pretty universal experience, whether it’s as simple as needing guidance on what to wear on a first date or as complex as wondering how you stack up in an increasingly hot dating pool. There are, however, some people who seem to see past the veil of mystery when it comes to dating, and our latest Playboy Advisor is certainly one of them. Here, Blaine Anderson, the matchmaker and dating coach behind Dating By Blaine, answers your biggest questions on love and dating.

I think I’m a nice, pretty good looking guy; I have a job, my own place, and all my female friends say I’m a catch. Still, I can’t seem to land a girlfriend. I go on plenty of dates, but they never lead to more than a few nice nights before fizzling out. What am I doing wrong?

Based on how you framed the question, I suspect you might be overweighing the value of your dating “résumé” versus creating romantic connections on dates.

Yes, being a catch on paper helps. Having a good job and your own place (and female friends) is great. But those things don’t create chemistry. If your dates go fine but then relationships stall, chances are women aren’t feeling an emotional pull, or “spark.” That often boils down to how you’re showing up on dates.

Are you flirting, or just making nice conversation? Are you expressing genuine interest and intent, or waiting for her to make decisions? Basically, are you setting the tone and pace for your dates, or just hoping something clicks?

Dating isn’t about proving you’re good enough. It’s about being intentional, curious, and bold enough to create romantic connections. Don’t treat dating as an audition, and instead focus on being present, and having fun. When you lead with charisma, not your qualifications, everything changes.

I hate dating. The whole process is exhausting to me, and I find myself sitting in awkward silence more often than I’d like to admit. How am I supposed to meet someone when dating feels like a death sentence?

If dating feels like a death sentence, stop dating. Instead of trying to push through the emotional fatigue of dating, give yourself permission to focus entirely on yourself for a while. What makes you feel good? What kind of life do you want to be living, regardless of who’s in it? Lean into those things. Pick up hobbies that make you curious. Spend time with friends who make you laugh. Get outside more. Cook something new. Build a world that feels more full before you resume dating.

Dating doesn’t need to be your focus right now. When you feel like dating sounds fun again, you can step back in. Particularly as a man, there isn’t much of a ticking clock, beyond whatever pressure you’re choosing to put on yourself to find someone right now.

Often, the best way to find connection is to stop looking so hard, and start living your best life solo. Try it, see what happens, and you might be pleasantly surprised with how the next few months unfold.

I’m a single guy and I go out with my friends a lot. We go to bars, basketball games, concerts—a ton of different places with a lot of different people. I’d love to meet a woman when I’m out, rather than relying on dating apps. How can I make a move when I see someone I’m interested in?

First off, props for building a social life where you’re out and about often with friends. It may not sound like an accomplishment, but you’re already way ahead of the curve, both because it sounds like you have a lot of opportunities to meet women, and because it sounds like you have good things going in your life, which is always attractive.

The #1 key to actually meeting women (and landing dates) from here is to stop worrying about the details of how you’ll approach, and start making friendly conversations as often as possible when you’re out.

Just walk up and say, “Hey, I don’t think we’ve met, and I think you’re cute, so I wanted to introduce myself…” whenever you spot a woman you’re attracted to in any of the environments you mentioned. This line is amazing because it’s simple, it’s authentic, and it shows intent, which is always a good thing in dating.

I don’t have a ton of dating experience, in part because I’m worried about seeming like a creep when I approach women. I want to be flirtatious, but how can I talk to women without making them feel uncomfortable?

The fact that you care about being respectful already puts you in a great place. The guys who worry about being creepy? They’re usually not the creepy ones!

The most important thing to remember about approaching women is that single women want to be approached by single men. I surveyed over 13,000 single women in the U.S. and U.K. in January of 2024, and literally 95% said they wish they were approached IRL more often!

Every guy has (or imagines) a horror story about a woman reacting badly to being approached, but as long as you’re being friendly and respectful, bad reactions are actually super uncommon in my experience.

Aim for confident, kind, and curious—not performative or pushy—and no one will think you’re a creep. This doesn’t guarantee that any given woman you approach will be romantically interested, in fact, most won’t be. But women are unlikely to be uncomfortable when you approach at the least.

Best practices: Don’t approach from behind. Don’t touch someone you don’t know. Smile. Make eye contact. Say something simple and situational. If a woman seems open to you (she’s asking questions back, smiling, not rushing to get away), you should ask her out. If she’s not interested? No big deal. Say, “No sweat. Nice chatting with you, have a great day,” and move on.

There are so many people on dating apps, I don’t know what would make a woman choose me. There’s bound to be a taller, richer, better looking guy. How can I stand out with so much competition?

Honest answer? Stop using dating apps! You’re spot on that competition is fierce dating online, and the mechanics of swiping tend to reward just a small handful of the tallest or most conventionally handsome guys.

You can absolutely improve your matches online with high-quality photos and playful prompts, but I’m increasingly a believer that the investment required to make a truly great profile (and then subsequently swipe and lead conversations in hopes of landing a date) isn’t worth it for most guys.

If you invest the same amount of time and effort into meeting women IRL, you’ll wind up with way better outcomes, and way more confidence. Basically, spend less time on Hinge, and spend more time wherever women you like are hanging out.

What am I supposed to wear on a date? I don’t want to look like I’m trying too hard, but also I want to show that I care. What’s the right level of dressed up?

Remember that if a woman has already agreed to meet up with you for a date, she’s already interested in you. You don’t need to impress her with your clothes, you just want to look presentable.

Don’t dress up, so much as make sure your clothes (1) fit your body, (2) are appropriate for the environment, and (3) are well maintained. Style is personal, and there are so many different “good” first date outfits that I almost hesitate to say this, but a crisp pair of jeans, a crisp t-shirt, and a nice overshirt or jacket are perfect for 95% of first dates!

I went on a date with a woman recently and it went really well. We had fun together, and had sex that night. Even though she was great, I’m not interested in a relationship. Am I an asshole if I never text her again?

Whether you’re an asshole depends on several missing details (e.g. in what context did you originally meet? Do you think she expects more than just a one-night stand?)

All else equal, I’m not sure it makes you more of an asshole if you don’t text her, versus if you proactively send her a “Great meeting you, but we’re not a fit…” message.

For all you know, she may not want to see you again either, so I don’t think proactively texting her is essential in this situation. But if you feel confident she’d want to see you again (e.g. you’re certain she’ll text you if you don’t text her) it’s probably best to just shoot her a polite message now, so she’s not waiting around.

The only way to guarantee you’re an asshole is if she reaches out, and then you don’t respond. Ghosting is lame, and karma will eventually bite you in the ass. Don’t ghost.

I like to flirt with women online, but when it comes time to actually set a date, I lose interest. I don’t know why I don’t want to take things offline. Is this shitty of me? What should I do instead?

That sounds a little shitty, both for the women you’re leading on, and for yourself.

Is staring at your phone to flirt with women you’ll never actually meet really how you want to be spending your time? Perhaps it feels fun in the moment, but I’d imagine heroin feels fun in the moment, too….

Purely out of self interest, consider new hobbies, and at the least, explore why you don’t want to “take things offline.”

I’m not a very confident guy, and it really shows when it comes to sex. I’ve had some luck in the dating field, but I often cut things off before we get close to having sex because I’m insecure about my body. I feel like I’m supposed to be the one chasing sex, but often I’m shying away from it. What’s wrong with me?

This isn’t uncommon. From what you shared, it sounds like women find you sexually attractive, so the biggest thing that’s “wrong” with you is your self-image. Why do you feel insecure about your body? Lead yourself all the way down the uncomfortable chain of questions (i.e. continue to ask yourself “why”) until you identify the root cause. It’s worth struggling with, because what you discover at the bottom may surprise you and set you free.

I’d add that part of the solution may involve changing your body. In my experience, most guys with body image issues wind up happiest if they both (A) stop beating themselves up mentally for not looking perfect, and (B) build better eating and gym habits. Obviously everyone’s situation is different, but I share this because I hear advice like “you just need to accept yourself” all the time. Depending on what kind of shape you’re in, you may not want to accept the status quo, and you may want to make physical changes.

I’ve been seeing this great girl for a few months. It started casually, but lately we can’t seem to get enough of each other. We spend days on end together, and I want to make things official. How soon is too soon to lock things down? How do I even start that conversation?

Assuming you’re both high-functioning independent adults, the right time to have the “lock things down” conversation — or whatever you want to call it — with a woman tends to be around the time you’ve been on a successful overnight trip together.

Before this point, you probably don’t know enough about her to make an informed decision. Travel reveals a lot! After this point, you both probably have enough information to decide whether you want to continue seeing each other, and punting the conversation further seems like a waste of time to me.

Assuming you’re indeed at the right stage of your relationship, best practice is to wait for an emotional high note (e.g. you’re enjoying dinner together) and then genuinely state your purpose without placing a huge expectation on her.

For example, you could say, “I’ve loved getting to know you, and I want to continue getting to know you. What would you think about being exclusive together?”

This isn’t fancy, but it will get the job done. Good luck!