Dating can be tough. First dates—and figuring out where to go, what to do, what to say (what not to say), or what to wear? Even tougher.
In fact, navigating the modern-day dating era is difficult for just about everyone: men and women, people of all ages, and even those who write about sex and relationships for a living.
Here, MensHealth.com’s digital fitness editor Brett Williams and Rosa Heyman, deputy editor for Cosmopolitan, reveal how they go about the first date, including the first things they notice, how they prep, as well as do’s, don’ts, and what they think about the first date kiss.
On first impressions…
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Rosa: This might make me seem shallow, but I notice someone’s appearance and how they carry themselves—the clothes that they’re wearing, and if they’re smiling.
Brett: I don’t think there’s anything shallow about that. That’s really all you have to go off, right? Appearance is heightened. There’s that initial moment when you walk in and see how seriously the person is taking this encounter.
On prepping for the date…
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Brett: I typically will make sure that it looks like I put some effort into my appearance. I don’t want to be too try-hard. I’d wear something slightly nicer than what I’d wear to work, but it depends on what we’re doing. Then, I just make sure I’m clean and that I smell good. We’re pretty lucky as guys that we have that as the bar. I’m not a huge cologne guy—I don’t need spray and sprays and sprays, just two: one spray of BOSS The Scent on the inside of my shirt, one on the outside. You don’t want to be sitting there and have the person thinking about how strong you smell, but you do want there to be a nice smell.
Rosa: I also like to have a glass of wine. It’s a good unwinding tactic for me. Then I’ll brush my teeth and touch up my makeup.
Brett: I think the best way to prepare, honestly, is just to remind yourself you’re meeting someone and it’s supposed to be fun.
Rosa: Getting in a good headspace is important.
On do’s and don’ts…
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Rosa: I’ll ask people a lot about themselves and I hate it when people do not return any interest. It’s not that I want to talk about myself—I just want to feel like I’m not an interviewer at a college admissions office.
Brett: An obvious don’t would also be: Don’t be an asshole to the people serving you.
Rosa: I also don’t like when people are on their phones a lot.
Rosa: Sometimes, I’ll hear people come on really strong about something without testing my feelings about it first. Then you get into something you fundamentally disagree on. That can be really awkward.
Brett: Lying. Don’t go along with something the other person is saying just because you want them to like you. It’s one thing not to want to rock the boat, but if it matters, there’s no reason to go along with it.
Rosa: To your point about honesty, there are certain things you can avoid on your first date, too.
Brett: Don’t bring up exes.
Rosa: I think if I had a child I might bring that up. There are certain things you should tell the other person. And I think you should feel free to be honest about how you felt about the date.
Rosa: For do’s, I think any kind of activity where you do something that’s not just sitting across the table from someone going through your resume would be fun. You can get to know someone through an organic activity.
Brett: I prefer the sit-down. And I think you want a place that’s not going to be super loud, with enough things on the drink menu, and you want somewhere that’s not super far away either.
On who should pay…
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Rosa: I think that whoever asks should offer to pay. If I ask someone out, I think I would offer to pay. But I think everyone should split the bill on a first date.
Brett: I wouldn’t press the issue. I was raised much more in terms of gender politics. I grew up paying for everything. When I’ve dated outside of that, I would always wait until the bill came and if there was no offer, I would just pay. Many women are assertive enough to say “let’s split this,” and almost every date I’ve had in the past few years has been a split.
Rosa: Especially first dates. I wouldn’t want to feel like I owed him anything.
Brett: There’s a weird power imbalance that comes with that.
Rosa: Especially if I wasn’t interested in the person.
When to connect off the app or when to text after the date…
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Brett: After the first date, if it goes well. The first time I ever dated somebody off of an app that’s what we did. That’s an actual indicator that someone does want to see you again.
Rosa: I totally agree. If I was into someone enough to go on a date with them I’d probably be willing to give my number. In terms of after the date, I want to receive a text the next day if I’m into the person.
Brett: It depends. There have been times I’ve been really amped up. I might text the same night to say “I had a really good time,” or “Did you get home safe?” That type of text shouldn’t be a leading text to begin a conversation. I would probably text the person the next afternoon, depending on how good of a time I had.
Rosa: I do think it’s weird if you went on a date and you were really vibing and you don’t hear from someone for three days.
Brett: Yes that convention should die; we all have cell phones!
Rosa: It makes it feel weird if you don’t acknowledge that you just spent three hours of your life together.
On kissing…
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Rosa: If I’m into the person, I want to kiss on the first date. It’s another test on the rubric of whether I want to continue this.
Brett: I have no qualms about kissing on a first date. I don’t think it’s weird at all. I don’t have anything against someone who doesn’t want to do it though.
Rosa: I like to do it!
Brett: Do whatever you want with someone as long as they’re consenting and you’re having a good time. I also feel like whether or not you kiss someone should not be a barometer for a good date or not. It can’t all hinge on a kiss.
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