20 Questions to Ask Before Dating Him

Over the years, as a gay man on the Internet, I have come up with 20 Questions that help me to judge whether or not a guy is worthy of a date with me. It has helped me in so many situations in the past and so I wanted to offer them to you, so you can put them to good use and maybe they will help someone else too. Of course, each of these questions is pertinent to myself, and so if you have other things you would like to ask, switch them out, or add to your own list of 20 Questions to ask a guy before asking him out on a date.

1. Do you have a job? Sounds pretty simple, doesn’t it? But a guy without a job, who is spending all of his time online looking for dick, doesn’t really sound like someone worthy of dating. How is he going to afford taking you out to dinner, or buying you that bottle of poppers for your hot date night?
2. Where are you from? It is important to find out if you speak the same language, or have the same societal expectations. If you’re from two different worlds, having a basic conversation may not be possible. Personally, if I am looking to date someone, it’s a waste of time to chat online with someone who lives thousands of miles away.
3. Do you live alone?
   Personally, I am looking for someone single to date myself. I’m not looking to be someone’s trick or side-hustle. I’m also not looking to date a guy who lives with his parents. I’m way too old to be sneaking in and out of his bedroom at night. And a guy who won’t have you over to his place because his “roommate is home,” probably has a relationship with the guy he’s worried about you meeting.
4. What are you into? Sounds pretty basic, right? But if you don’t know what you want, then how am I supposed to know how to make you feel good? Also, if you’re into some pretty weird stuff, I’d like to know up front rather than find out when it’s too late.
5. Are you Top or Bottom? Some guys are versatile and some prefer one or the other, but it is pretty important to find this out right from the start, since we all have our preferences.
6. What is your status? It is very important to know whether or not the person you are going to have sex with is HIV positive or not. It is also to know whether he has any other STI’s, including Hepatitis C. Depending on how he answers this question, really can tell a lot about him. If he doesn’t know his status, pass him by. It means that he doesn’t care about his own health, and that is not sexy.
7. How hung are you? It’s always nice to know whether or not your potential date has the goods to make you feel good. But if a guy is TOO BIG for your britches, you may not want to get torn up or hurt.
8. What kind of kink are you into? Some guys are passionate and into hot n’ heavy sex, but may not be into kink or any fetishes. Depending on what you’re into, it is important to ask and figure out if you are both on the same page, to avoid any uncomfortable situations.
9. What are you looking for? This will help you figure out if the guy you are interested in, has an interest in dating you, or if he just wants to have sex with you. He may also be looking for no-strings or anonymous sex. That’s good to know!
10. What makes you feel good? Some guys may just be into oral, whereas others may want to get down and dirty. It is good to find out whether or not the guy wants to get piggy or just hang out and stroke it, saving you time and hassle in the end.
11. How do you like to fuck? Once you have figured out if a guy wants to top you or bottom for you, you may want to ask how he likes it. This will give you a good idea of whether or not you can handle his desires, as well as prepare for what is to come.
12. Are you a smoker? Personally, I prefer a guy who is not a smoker. While it is not a deal-breaker, if he is a smoker, I can request that he brushes his teeth and uses mouthwash before we hook up. If he is a gentleman, he’ll do that anyway. Keep in mind, guys who smoke may experience a problem with erectile dysfunction due to the lower amount of oxygen flow in their bodies.
13. Are you a drinker? While a few beers on a date may be alright, for most guys, getting shitfaced on a date and then trying to stick it in, does not sound like a fun time. Sober sex is incredibly hot! But you also don’t want to end up dating a drunk or an alcoholic who can’t handle himself.
14. Do you like to party? While this should be my number one question, this is often quite easily answered by the a capital T in their profile or just by their intentions. Most guys who are looking to PnP (Party n’ Play) are seeking that themselves, so they will generally ask you up front. If you are not interested in doing drugs, or dating someone who is into drugs, then asking right out the door is your best option. But putting “No PnP” in your profile may help avoid those kinds of people.
15. How wild do you like to get? Depending on your mood, you may be into a casual romp in the bedroom, or you may want to pull out the sling and get really deeply involved. Knowing if they like to get wild and crazy, may help you avoid a big mistake, or you can line up some fun experiences for your future.
16. Do you like to kiss? Some guys have grown up with a stigma from being gay and may not enjoy kissing another man. This is important to find out, especially if you enjoy deep, heavy and passionate kisses.
17. Do you like it raw? So while you may know if he likes to top or bottom, asking if he likes it raw (without a condom) may be a sign of whether or not he is playing safe or not. If you prefer to have safer sex, then you need to be prepared to bring a condom and plan ahead. Don’t rely upon anyone else to make sure you are safe.
18. Are you into gear? If you are one of those guys who will only have sex while wearing your leather gear, then that’s cool for you, but personally, I enjoy hot, naked, sweaty, bodies writhing around on the bed. I enjoy guys in hot underwear, jock straps or singlets though, so asking about gear can lead into other questions.
19. Do you like poppers? Some guys enjoy poppers for bottoming and others don’t like them at all due to headaches. Other men should not participate due to medical conditions, so it may be beneficial to ask before using them with another person.
20. When was the last time you hooked up? While you may not want to date someone who never leaves his house, you also may not want to date someone who was last night’s bottom-breeding-party-whore at the local bathhouse. And finally… Is there anything you would like to ask me? After we’ve talked for a few days and I’ve asked all my 20 questions of him, at the same time, talking about myself and my needs and desires, you’d think we had gotten to know quite a bit about each other. The most important thing to find out though, is whether or not he is open, honest, up-front and compatible with you. It may be a red flag if he doesn’t care to ask about you. My 20 questions have often helped save me from having bad experiences or meeting the wrong people. And often times, I don’t even get through asking all 20 questions, but my point of this entire list, is to find guys who are willing to discuss themselves with you. This means they are open to actually getting to know someone, rather than simply trying to add another notch to their headboard.

Written by Dave, PIGSwap member.