Maybe every generation feels this way, but as a single gal, it seems to me that early-stage dating etiquette is more confusing and complicated than ever before. App culture, increasingly blurry gender roles, and other large societal shifts have transformed the basics of dating at a pace so rapid, single people of all ages are struggling to keep up. It’s not uncommon, by way of an example, for me to remark to a friend, He let me split the check, and then follow-up this maybe-complaint quickly with, But that’s cool, right?”
Who’s paying is, of course, only the tip of the dating etiquette iceberg. Am I being overly cautious if I refuse a first-date hang at his place? Emasculating if I offer to split the check? Anti-feminist if I don’t? How soon should I mention that I’m vegan, or keto, or sober, or breatharian (j/k), or whatever the case may be? What about (gulp) my take on marriage and children?
While the answers to such questions are, ultimately, personal, experts from matchmaking firms The BEVY and Three Day Rule, along with an insider from the female-forward swipe-based app Bumble, weigh in on these and more early-stage dating topics below. Armed with their advice, you may find the courtship game becomes less stressful—because it’s hard enough to navigate profile red flags and deal with date-night breakout drama, isn’t it?
Here’s all you need to know about navigating the ever-changing dating world.
Who pays for the date?
“We see this question come up all the time—men are afraid to insult an independent woman by insisting on paying the bill,” says Three Day Rule founder Talia Goldstein. “Trust us, guys, you’re not.” Word. She believes that just because women can pay the check, this doesn’t mean they should. The BEVY founders Greta Tufvesson and Nikki Lewis agree: “Call us old fashioned, but we like to say chivalry isn’t dead—if a man asks you out, he should pay,” Tufvesson tells me.
That being said, if you continue to date, you shouldn’t expect your plus-one to pay every tab. “Treat him or her to drinks another time, pick up the cab fare on your way to dinner together, or buy lunch,” Lewis suggests. “I’ve never heard a guy wary of a woman who didn’t offer to split the bill on a first date, but I’ve definitely heard a guy complain about dating a woman who never once took out her wallet after some real time spent together.”
To eliminate some of the guesswork after the first date, keep this rule in mind: “Whoever asks the person out should pay for the date,” Lewis says. If you’re the askee, it’s also okay to split the check if you’re comfortable with doing so—but it’s just as okay to simply and sincerely thank your date for the evening without the offer. “What’s most important isn’t whether you reach for your wallet or not,” Goldstein says. “It’s your reaction. If your date does offer to pick up the bill, be sure to say thank you… and mean it!”
Who plans the date?
“Women constantly ask us to find them a guy who is decisive, reliable, and a good planner,” Goldstein says. “The easiest way to display these qualities? Simply plan the date.” Amen, sister. If you or bae feel pressure in such a situation, however, signing up with The BEVY may offer the solution. The company plans all dates for its participants. (Typically, cocktails.)
Meanwhile, Alex Williamson el-Effendi, Bumble’s head of brand, says it doesn’t really matter who plans the date, and that if you have a great idea, go for it. However, she offers a caveat. “Be comfortable covering the cost if you create the plan,” she says.
Early dates at home—yay or nay?
Ladies, if you frequent certain dating apps, you know this is a thing, and personally, I hate it—especially when it’s suggested as a first-ever hang. No thank you, I tend to think. I saw that after-school special.
On this one, my experts agree that it depends entirely on what you’re comfortable with doing, but that you should meet in a public place first for safety reasons. “As long as you feel genuinely safe, do what you want to do,” Williamson el-Effendi says. Tufvesson’s take is a little more conservative—she recommends waiting until at least the third date to check out your crush’s digs. “You’ve gone on two dates and now you’re looking to get more intimate,” she explains. “This can be physical, but more importantly, you kind of just want to see where your date lives and size him or her up!”
And what should happen once you get there? “If you are dating at the house, have a fun plan in place so it doesn’t simply turn into the infamous Netflix and chill,” Goldstein says. “Cook dinner together, play a game, actually watch a movie, etc.” Lewis agrees, adding that you should not now—or ever—feel as though you’re expected to do anything sexual. Period.
How soon do you need to mention dietary and alcohol restrictions?
I recently planned a date with a guy who is both vegetarian and sober, which is 100 percent cool by me. However, his contribution to “planning” was something along the lines of Where should we go? I’m also watching sugar and carbs right now. (Eye roll.) His restrictions couldn’t matter any less to me, but since he was the one with a long list of no’s, I felt that he should have been proactive about researching a place he could eat—and I likely wouldn’t have been any wiser to the details of his diet.
According to Goldstein, that would have been the right approach to take. “These are things that are likely to come out on a first or second date just based on the context,” she says. “The important thing is to keep the conversation light and casual. Don’t make mountains out of molehills, as a simple No, I don’t drink or I’m actually a vegetarian should be plenty sufficient.”
The BEVY founders take a slightly different perspective on this. “Restrictions and preferences are crucial and should be brought up before the first date,” Tufvesson says. “Not drinking or eating certain things can be a major deal-breaker in relationships, especially since you’ll ideally be enjoying meals with your partner for the rest of your life.”
Williamson el-Effendi also suggests being upfront about your restrictions, but for another reason. “You want to spend your time with someone who appreciates you for you,” she says. “Don’t hide who you are for the sake of a good date—if you’re vegan, be vegan.”
Are there any “don’ts” in terms of texting in early-stage dating?
Although it’s totally common (and fun!) to banter over text, experts say that over-communicating is not so great early on. “Remember, you barely know this person,” Goldstein says, adding that excessive back-and-forth before a first date can lead to unrealistic expectations followed by a letdown once you meet in person.
Tufvesson and Lewis offer specific, date-by-date guidelines to further clarify this point. “[Before a first date], texting should just be to say you’re looking forward to meeting, and confirming you’re still on,” Lewis says. “After the first date, thanking someone for their time or drinks is appreciated, whether you plan on seeing them again or not.” If you are interested, they say, flirt a little but keep it to a minimum. “You don’t want him or her to think you have nothing going on in your life, even if you can’t stop thinking about them,” Tufvesson advises.
On the flip side of all of this, Goldstein cautions that you shouldn’t judge the person you’re dating on their text etiquette or digital eptitude. “It’s not a fair representation of who they are as a person,” she says, before offering one final text-related warning. “Steer clear of either providing selfies or asking for selfies before you meet up.” (Maybe send them an artistic shot of the guacamole from your girls’ night out instead?)
How should you break something off early in the game?
If you’re anything like me, you feel irrationally guilty ending things with any guy or gal, no matter how long you’ve been dating. Sometimes, it can feel easiest just to try to ghost, but Goldstein says doing so is never the way to go. “An upfront, respectful, honest text is all you need, and in this crazy world of ghosting, it’s incredibly well-received and respected,” she says. Her suggestion is that you tell them you enjoyed meeting them and think they’re a catch, but that you simply didn’t feel a connection.
Tufvesson and Lewis are on board with this strategy. “We encourage honesty and adhere to cutting ties before it gets even harder,” Lewis says. “We’re all adults here, and when it comes to dating, you need to be sincere but also upfront so you can move forward.”
How soon is it okay to discuss the future?
Both The BEVY and Three Day Rule pre-screen for goals like marriage and kids, so that whoever you’re meeting is already on the same page as you. But they don’t believe you should take on that role—at least, not on the first few dates. “We get it, you want to date with intention,” Goldstein says. “In the real world, however, bringing up babies on a first date is just too much.”
She instead suggests that you find creative ways to infer your goals without pointing directly at the ticking clock hanging over your head. “Have nieces and nephews that you love spending time with or admire your parents’ longstanding marriage? These are great ways to introduce these ideas without getting too ahead of yourself,” she offers.
Tufvesson and Lewis say—whether it was a matchup or a regular set up—these questions should be fair game by date three or four and offer one exception to the rule. “If you have been married or already have babies, that is something you should definitely mention from the get-go,” Tufvesson says.
Should you kiss on the first date? And does it mean something if he/she doesn’t go for it?
The answer to the first question, according to my experts, is pretty simply If you want to, go for it. While the answer to the latter, on the other hand, is Probably not.
If you were hoping for a make-out sesh but were left with a cheek peck, both The BEVY gals and Goldstein say your date could have been nervous or uncertain about your interest level. “[If you’re into it], initiate by being clear with your body language,” Goldstein recommends. “Actions speak louder than anything, so lean in when you’re speaking with him, or perhaps playfully put your hand on his arm or knee.” You can also learn to read your date’s flirting cues—and know that if there’s hair-touching and eye contact involved, you can safely prepare for a smooch after last call.
Nervous to bring up dietary restrictions with your new bae? Apparently, being vegetarian or vegan could make you more successful on the dating market. Being an exercise junkie might, too.
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