This is the censored version of this post on dating. You can view its uncensored version with sexually explicit (NSFW) photos on Pillowfort.

At some point, bi+ guys end up going on a date with a person of a different gender than what they’re used to. This tends to happen when a guy has only ever dated women, or only men. Or maybe you’ve dated very little, and the prospect intimidates you. These pointers can help make this an enjoyable experience and avoid some missteps.

Asking someone out

This is the part a lot of people find the hardest, and we’re not even on the actual date. In a nutshell: mind the context; pay attention to signals the person has been sending you; say what you want directly; but make it clear the person can decline and leave room for a graceful exit.

Context means accounting for the situation through which you know the person, as well as any existing power dynamics. Asking a friend or an acquaintance out is different than asking a coworker, or someone who’s in a hierarchical relationship with you. That last one is often a bad idea. It might be forbidden by the organization’s rules, or flat-out illegal in some situations.

Likewise, women and people who are seen as such get a lot of unwanted sexual attention. So when you ask a woman out, or a nonbinary or trans person who was assigned female at birth, acknowledge that and act accordingly.

For example, you could make your approach with “I know you probably get a lot of unwanted attention from guys and feel free to say no, but I really like [this] and [this] about you, and I wanted to know if you’d like to go out sometime.” This is less of an issue with cisgender men and to some extent transgender men. Still, make it clear that it’s fine for the person to say no, and give them the chance to do so subtly and politely.

Notice the signals

Also, before making an ask, pay attention to the signals they’ve been sending you. Does the person smile a lot when they’re interacting with you? Do they make a lot of eye contact? Or are they keeping some distance and boundaries with you? If you notice the latter, they will probably turn you down. But some people are just shy and awkward, and they might be delighted you’re taking the first steps. Still, when someone seems closed to an ask, give them even more chance to back out with grace.

Finally, even if you notice positive signals from the person, they could say no for reasons that have little to do with you. They might like you, but not that way. Maybe they’re not on the market for dating, or they’re too busy. Or when it’s another man, maybe they’re not ready to date another guy.

A female and a male student chat animatedly in front of their school building. They both seem to be enjoying the conversation. To end up dating, you first need to ask!

Dating acquaintances, friends and folks you’ve just met

Still, asking an acquaintance or a friend out is different than asking someone you’ve just met. When you have a potential romantic interest in an acquaintance, I suggest you ask them out sooner rather than later. If things might not work out, you’d rather know before you get too infatuated with them.

When they’re a long-time friend, be aware it can impact your friendship. Yet strong friendships can survive the realization that one of you wants something different than the other, as long as you respect a no. It’s fair too to take some time and space to process your disappointment and heal before you resume the friendship.

Asking someone out that you’ve just met is lower stakes, but mind the power dynamics I’ve mentioned above. Expect cis men in a queer setting to react better to being asked out of the blue, given the culture of cruising many are used to. Yet no matter who the person is, don’t be a creep. Once again, give them the chance to make an elegant exit.

The ask

A good ask could sound like, “Hey, I know this is sudden and that you might get unwanted attention from guys, but I really dig your style and I’d like the chance to get to know you better. You don’t have to respond to this, but here’s my number if you ever feel like texting me to chat and maybe go out.”

Let’s say things are looking good and the person says they’re interested to go out on a date with you. Then it’s best to arrange right away what you will be doing together, the place and the time. It’s easier too to ask someone out by proposing a concrete activity instead of just asking if they’ll go on a date with you. When you don’t know the person very much, you should ask what kind of stuff they like doing. See if there’s something you both like that you could do.

You can’t make someone like you

A lot of guys think flirting, wooing, and dating are attempts to win the person over or to get them to like you. But you can’t make someone like you. When they find you attractive and they like your personality, the potential for a connection is already there. But when they don’t, you can’t change that, and you will create uncomfortable situations if you try to.

It’s disappointing to realize someone you like isn’t into you, and it’s okay to feel that way. Still, you can’t change that, and it’s better to move on. Feelings people have for each other can change over time: there are many stories of platonic friends eventually discovering a romantic connection. But it’s not the result of trying to get someone to like you. It’s just intimacy deepening over time—and often it just doesn’t happen. You will break your heart pining over someone who doesn’t reciprocate your affection in the hope that it will change someday, especially when it’s a heterosexual man.

“The guy should show he really wants you before you say yes!”

Some people with old-fashioned values though expect their suitor to woo and court them, and to be insistent. This creates a dangerous situation, however, in which you can’t know what’s going on. You can easily cross a line into harassment when you read the situation wrong. As a rule, I’d advise you to not get involved sexually or romantically with someone who doesn’t want to say what they want. These games just create drama and sometimes worse situations.

Finally, while you can’t get someone to like you, you can ruin things with someone who actually liked you. Trying too hard, putting pressure on them, or acting like a creep will do that, especially with women. So make your peace with the fact that a lot of the time, the other person just won’t be into you; it comes with asking people out. But unless there is something very wrong with your appearance or your behaviour, there will be people who are into you, and you’ll meet them someday.

The actual date

My #1 dating advice

Don’t see this as a date. You’re two people hanging out, or getting together for a movie, a dinner, or a brew. Maybe sexy times are in the cards; maybe they aren’t. The more you see this as just two persons hanging out to get to know each other, the less stressed out you’re going to be, and the better of a time you’re going to have. The gender of the person you’re going out with doesn’t matter for this – my best dates have been in that mindset. Frankly, I think it’s the secret to the whole thing – people make a much bigger deal out of dating than it needs to be.

The cliche: be yourself

But be the nice, presentable version of yourself, not the Foul Bachelor Frog version. Still, don’t put up a facade or a front. If your dating partner is going to like you, you want them to like you for who you are. So be genuine.

The Foul Bachelor Frog meme. Captions read, "First date in forever, cleans dick." The word "dick" is mostly redacted by a pink rectangle with the "censored" on it. Hygiene matters when dating!

Hygiene and clothes

For these, be on the ball, but don’t overdo it. Shower and clean your genitals. Go easy on the deodorant, cologne or the aftershave. Wear nice undies, but no need for those $40 trunks unless that’s your thing. I wear Joe Boxer boxer briefs, and it’s never stopped me from getting laid. Put on clothes in which you feel comfortable and that make you look great, but don’t overdress – you risk intimidating the other person. Think casual unless the two of you decided to go someplace swanky, or you love to dress sharp.

Be savvy about gender identity

The person you’re about to hang out with could be trans and you might not know about it, or they could have more complex views of their own gender than what you’re used to. You might be starting to hang out in queer circles when your date is not a cisgender woman. This means you’ll run into people with diverse gender identities.

This is a huge topic. I can’t cover it all here, and I’m not the ideal person to do it. This short guide covers the important basics, with links to other resources at the end. Give it a read, in case someone you’re going out with comes out to you as trans. When you do know you are going on a date with a trans person, brush up on your manners as a trans ally.

Dating when you’re a trans or nonbinary guy

The biggest question on your mind might be when to come out to that other person you might end up seeing on a regular basis, assuming you aren’t out already. It’s a big deal. Besides the possibility of rejection, coming out could at times put you in danger, especially if you’re trans.

Even when that other person means well, they might know little about how to be a good trans or nonbinary ally. They could speak or behave in ways that are not cool or that could trigger feelings of dysphoria. There’s the risk too of them outing you to other people you both know. The decision to come out belongs to you, and you don’t owe it to anyone.

Taking longer to come out means you have more time to decide how safe coming out to that person is. They will also get to know you as a person before they have to face any prejudices they might have against trans or nonbinary people. On the other hand, the emotional stakes become higher. You have to deal longer with the anxiety of being closeted. In a dating context, you might feel that the longer you take to come out, the harder it is to do so. Still, trust your gut and your judgment.

Coming out as a bi+ guy to a dating partner

Speaking of coming out, a lot of people wonder when and how to bring up their sexuality with a new dating partner. I would say the sooner the better, without making it look forced. Get it out of the way before either of you gets emotionally attached. Your dating partner could turn out to be a biphobic or monosexist a**hole.

As most people meet dating partners online these days, you should put your sexual orientation in your profile if you’re comfortable with that. For people who are fine with having a visible marker, you can have a pin that says something about your orientation, or you can wear the bi colours—pink, purple and blue. Many people miss or misinterpret subtle markers, though; some people have mistaken my “BI” pin as standing for Business Intelligence. . .

When each other’s dating or previous partner history comes up, it’s a good time to mention that you like different genders and that you’ve been with people who aren’t the same gender as this dating partner. Don’t spend too much time talking about exes, though, that’s risky territory early on. Along a similar line, you can ask your partner if they’re only into men or if they like other genders too. This opens the door to saying more about your own orientation and experiences after that.

If you haven’t had the chance to come out and discuss each other’s orientation by the third time you see each other, it’s time to have that talk. You don’t want to get too invested in this exciting new relationship, just to discover they’re biphobic.

Biphobia and monosexism when dating

These can rear their ugly head in the dating game. Most of us have heard the words “I wouldn’t date a bi guy; I’m too afraid they’d leave me for a man/woman.” These situations suck. Those prejudices can come from any dating partner, even queer ones. Sometimes they even come from other bi people—internalized biphobia is a thing.

You should be aware too that you’re more likely to run into this with heterosexual women, unfortunately. In a 2016 survey from Glamour, 63% of women said they wouldn’t date a man who’s had sex with another man. This wasn’t just for bi men, but for any man who has experimented with another guy, even once. Some bi+ guys choose to limit their dating pool to queer people for that reason.

When someone treats you poorly because of their biphobia, try to find some people who embrace your sexual orientation for support, even if it’s just online.

Three menacing Daleks from the show Doctor Who, silk-screened on a lavender background. Captions read, "Exterminate monosexism."

Your physical safety on a date

When you get together for the first time with someone you’ve met online—another man especially—you can take a few steps to protect your safety. Since we can face homophobia, biphobia or transphobia, we need to be more careful about physical safety than most people. The risk depends on where you live and in many cases, you might feel these steps are unnecessary. I’m giving the tips in case you ever feel you need them.

  • Meet in a public space first.
  • Spend some time talking with the person before you head to a private place like their home or yours.
  • Trust your gut – when you get a bad feeling about things, excuse yourself and leave.
  • Let a trusted person know you’re meeting someone you met online. If your date is another guy, it’s more difficult to let a friend know when you’re in the closet, but you can still describe the encounter as platonic.
  • Agree to check in with that friend once in a while, and text them the address of any place you end up going, especially when you expect to be alone with your date.

How to be a decent conversationalist

You have two ears, but only one mouth – so listen more than you talk. Ask questions. Show genuine interest in what the other person has to say, in who they are. Listen. Say your piece when it’s appropriate, but keep the balance tilted in favour of listening to your dating partner rather than talking about yourself.

On sexual innuendo when dating

A lot of queer guys love sexual innuendo, even more so when they’re interested in what’s in the pants of the person they’re chatting up. Personally, it’s something I like about hanging out with queers: the relaxed, casual flirting and slinging of sexual innuendo. Not everyone is like that, though. How comfortable someone is with sex varies from one person to another. But one of the things many queer guys love from spending time with each other is that we have permission to acknowledge that yeah, many of us are a bunch of f***ing horndogs.

The innuendo doesn’t necessarily mean the other guy wants to end up in your bed. Sexual innuendo is fun in and of itself. Still, it’s one sign you guys are on the right track when that’s your plan, and it’s a good way of gauging interest. Plus, it’s liberating when you’re not used to expressing the homo end of your sexuality.

On the other hand, be more cautious with innuendo you direct at women and other AFAB people. It’s best to test the waters a bit before you do that, or to let them make the first move on that front. They could have had bad experiences with sexual harassment or with nasty gender power dynamics. Misplaced sexual innuendo can make you come across as a creep, or set off red flags.

Who pays for stuff?

When you’re two guys, you will usually agree to pay for your own things, split the bill, or alternate between buying rounds if it’s a bar date. Even on a date with a woman, I would be really uncomfortable assuming that I’d pay for her unless I was taking her out for her birthday or something. It’s the 21st century, people. I’d also expect nonbinary people to not be into that. Still, some folks are old-fashioned that way, so it’s best to clear up ahead of time what the expectations are.

When dating, be prepared for sex

If it’s important for you to use condoms, keep them with you at all times even when you don’t expect sex on a first date. Know how to use condoms properly too. If you use on-demand PrEP, take it a few hours before you got out. This will minimize side effects and give it time to take effect. You don’t know what will happen on your date, especially if substances are involved . . . or because you’re both horny. Also, bring lube along if you’re open to butt sex, or if you use lube for wanking.

When your date is with someone who has a uterus and you’re not used to that, think of preventing an unplanned pregnancy—condoms aren’t just for protecting the two of you from STIs. When the prospect of sex comes up, ask your partner what kind of contraception methods they use on their end. If the idea of an unplanned pregnancy terrifies you, combine condoms with another contraception method. Even not ejaculating inside your partner in addition to using a condom can do. Condoms are not as reliable as some other methods of contraception in day-to-day use, unless you know the ins-and-outs—so to speak—of using them perfectly.

Dating and using substances

Think about how much you want to use, and figure out whether the two of you are on the same page on this. A lot of bi+ guys like to drink or smoke pot. Some like stronger drugs on occasion, or often. Some people get together for the first time and have a lot of fun getting trashed together, especially when they’re both guys. Others don’t use at all. A conflict can happen though if the two of you have different values or expectations about substance use.

Also, when one of you, or both, is less comfortable with their sexuality, the temptation to use—and to use a lot—can be stronger, if just to feel less self-conscious. This happens especially with bi+ guys exploring same-sex experiences.

When you are planning on using, even if your plans involve only a social drink or joint, remember to:

  • pack condoms and lube ahead of time;
  • pace yourself, and remember that mixing substances often amplifies their effect;
  • and hold back from using to the point where you take sexual risks you would not have taken, or where one of you guys can’t consent anymore.

It’s not consensual sex if one of you is way too far gone, even when they’re the ones coming on to the other person. This can be a lot more complex and nuanced than that in reality. A drunk person can also sexually assault a sober person. Still, holding back from doing sexual stuff when someone is too far gone remains a good ground rule to keep. So make sure your date gets home safe, and give them a raincheck on that hot sex for when they have a better handle on the decisions they’re making.

Using to be able to have sex

If you’re using because you don’t think you could go through with sex with the other person, think twice about what you’re doing. I’m not judging. I had to get trashed on sambuca with the first guy I ever had sex with for us to go through with it. But it’s okay to feel vulnerable when you have those first sexual experiences. It’s even more true when it’s with someone whose gender is different from what you’re used to.

When it’s with another guy, there might be feelings of guilt or shame you haven’t worked through yet. That’s okay. Yet, it might be better to wait until you’re comfortable with someone to explore your sexuality together. You can share with them how the experience makes you feel, even the less pleasant stuff.

Glass shelves filled with liquor bottles. Captions read, "You should be getting whiskey, weed and a bong, but some legislatures hate fun. You get pretty liquor shelves instead, legal everywhere—almost."

To go, or not to go for the kiss?

When it comes to going for the kiss or not, there’s only one acceptable answer to that in my book: ask the other person first. Not everyone agrees on that one. Some people think talking “ruins the mood,” but I call bulls*** on that one. Consent and respect matter. Always make sure your partners are into what you want to try. Reassure them that a “no” or changing their mind in the middle of things are okay. It’s the same thing even in a situation in which you’re two guys.

But when your partner’s gender is different than yours, mind the gender power dynamics at play. You can just say: “I think you’re really hot. Do you want to make out, or that’s not something you want to do with me?” It’s easier to ask than what most people think.

Still, read body language before you ask. Is their posture open? Do they laugh easily with you? Is there a lot of eye contact? Some light touching? It’s a good sign when those are there, yet it’s no guarantee they’re into you that way. I’ve always asked people for permission to kiss them for the first time, even when their eyes were screaming at me to do it, and I was always glad I did.

Line drawing of two people kissing. One of them is getting a low-five from behind from a third person for getting there.

Sex on the first date

There’s a lot of judgment around having sex on the first date, or not. Spoilers: I’m a sex-on-the-first-date kinda guy. Sex is nice, and pleasure is good for you. Having sex on your first meeting with another person won’t spoil a potential future relationship with you.

We’re all human, and sometimes we lose interest in a person after we’ve gotten in their pants. But when there are affinities for a meaningful friendship or romantic relationship, shagging that person on your first encounter won’t ruin any of those affinities – quite the opposite. Sharing orgasms is a bonding experience. Getting lust out of the way lets us see better what we want with this person. I’ve shagged my future husband on our first date, and I’ve become good friends with a lot of people with whom I hooked up early on.

There are people who would judge you for putting out on the first date, but no one has any business doing so. It’s a sad thing to say, but shagging on the first date can be a good filter for judgmental people. If anyone would reject you for giving them sexual pleasure on your first meeting, I don’t think you want them in your life. Some people think withholding sex is a way of getting the other person to “prove” their genuine interest in you. You might yourself feel that way. But interest or love are things that can be only proven over time, and not in a matter of a few weeks or months.

“But… I want to wait!”

Now, if you want to become closer with a person—or at least get to know them a bit first—before you have any kind of sex with them, that’s fine. There are all kinds of good reasons to make that decision, and no one should treat you poorly for that.

The world of hook-up apps and the cruising scene with other men can make you feel you have to put out or else no one will be into you. Or these can make you feel your values on sex and relationships are unpopular. Still, a lot of people will respect your choices, especially when they like you as a person. Just be honest about your needs and present them early on, without being judgmental yourself about people who hook-up quickly,

Finally, it’s okay too to hold up on sex when you’re still uncomfortable about doing it with someone of a given gender. A lot of bi guys feel conflicting emotions when that possibility comes up, especially with another man. Honesty is the best policy in those situations, and you deserve someone who’ll support you through those new experiences. It’s okay to say, “This whole ‘having sex with a [insert the person’s gender or identity]’ thing is new to me, and I feel out of my depth. I’m really into you, but I want to know that I can stop or that we’ll take things slowly if I need to.”

Two shirtless guys are lying very close to each other, face to face. They gaze into each other's eyes and are smiling. Captions read, "This should be two naked men lying next to one another. You get two shirtless guys smiling to each other instead."

Often, it just doesn’t work out

The reality is that most of the dates on which you’ll go won’t lead to a romantic relationship, or even a hook-up. Dating is about getting to know the other person, and exploring whether there’s a connection there or not. But most of the time, there isn’t, and that’s okay; you enjoy dating a lot more once you’ve made peace with that.

Sometimes, a date doesn’t lead to a second meeting. At other times, one of the people excuses themselves early to cut the awkwardness short. This is all fine, and it comes with the territory. Someone can stand you up; the date is a no-show, and that sucks. You can’t do anything to prevent someone from doing this to you. On your end, though, you should let the other person know if you decide not to go, even when it’s awkward. It’s better than them going there for nothing, and it reflects better on you.

How to follow up

Sometimes though, the date was exciting and fun, and you want to see the person again. When should you follow up then? A lot of people used to have a rule of waiting three days before following up on a good date, just to avoid appearing too eager. Yet in our day and age, three days can easily come across as ghosting—cutting off conversation with no explanation. This often happens on dating and hook-up apps.

Let the other person know quickly that you had a good time and that you hope you see them again. But past this point, give them the opportunity of making the conversation happen. It will be a good indicator of how interested they are. It leaves room too for the connection to end with grace when it turns out the other person isn’t into you. A lot of people just won’t say that they didn’t have as good of a time as you did, which happens. Constantly contacting them when that’s the case just increases the awkwardness. But believe me, if they like you, you’ll hear back from them.

Keeping your expectations in check

Another thing you should be careful about getting attached too quickly. It’s easy to get excited after an enjoyable date, and that’s understandable. But you don’t know each other well yet—unless you were long-time friends—and it’s yet unclear how the other person feels about you. There’s still room for things not to work out, and you’ll be heartbroken if you attach yourself too quickly. It’s scary too for the other person when you break the “I love yous” out on date number 2 or 3. Take this young relationship one day at a time. If the two of you do like each other, things will work out.

Two guys kissing outdoors in a crowd, at what seems to be a kiss-in.

Hopefully, some of this stuff will put you in a better position to enjoy a successful date, or to take in stride a date that doesn’t work out. Have fun on your date!