What Are the Rules for Dating in 2025? A Luxury Matchmaker Spills the Tea

There have always been generational differences in how we date. When I started dating as a 2010s teenager, my mom lamented that my high school romance was a boy asking if I wanted to “hang out,” not go on a formal date.

But these days, it feels like the changes in dating aren’t just decade-by-decade, they’re year-by-year. For daters of any age, it can be tough to keep up.

That’s why we asked Lisa Goodman, Vice President at Selective Search Luxury Matchmaking, what the dating rules are for 2025. Lisa answered some of the biggest dating questions asked by singles of all ages.

Dating has become pretty equitable since the feminist movement, but traditional gender roles still have influence. Some people want to break free from those expectations though. So, can women ask out men?

“Yes!” Lisa told us. “Confidence and clarity are super attractive and a bit sexy.” That applies to people of all genders.

But, there is a caveat: “Being pushy or aggressive is not attractive,” Lisa warned. Again, this is true for everyone, but men may, unfortunately, be more likely to clock a woman’s directness as aggressiveness. 

“Read the room,” Lisa said. “Just letting him know you’re attracted to him might be the way to go. A man typically likes to be the pursuer in the relationship.” 

This isn’t to say that you can’t ask a man out directly, but you may be more successful in actually getting a date if you let him take the lead.

“Men typically pay on the first date,” Lisa said. “End of story.”

After the first date, you can find a financial structure that works best for you. 

My boyfriend and I tend to split major expenses 50-50, but we go back and forth treating each other for date nights. When a relationship starts, every couple is different. 

On the first date, paying is “a sign of generosity,” Lisa said. It’s good manners.

If the date is going poorly, you don’t necessarily need to follow the same rules (though you do, of course, need to keep being respectful). 

“If neither of you sees this going anywhere, you might decide to go Dutch and leave it at that,” Lisa said.

For same-sex couples or those outside the gender binary, a good rule of thumb is that whoever asked the other out on the date should pay. Again, it’s a great way to show your generosity.

Some singles worry that opening a door or pulling out a chair is too over the top for a date these days.

“They are not over-the-top!” Lisa said. “Oh my gosh. Gestures and thoughtfulness never go out of style.”

Even for progressive women, small, chivalrous gestures are attractive. They suggest that you’re constantly thinking of your date’s comfort. 

“Gestures and thoughtfulness never go out of style.” — Lisa

And bonus points if you do these gestures without drawing attention to them. When my boyfriend wordlessly switches to the curbside of the street when we’re on a walk, it makes me feel really loved.

On the flip side, if performing these gestures feels like a big production, your date will notice. 

“The only time it wouldn’t be so great is if you were faking it, if it’s not your style, it will come across as disingenuous,” Lisa said.

Many of my single friends feel that dating isn’t as fun as it used to be. They end up going on the same happy hour date or coffee date every week, and it becomes an interview. It rarely lasts longer than an hour.

Lisa says the problem isn’t the people, it’s the venue.

“Overwhelmingly, my vote is to take the time and take her to dinner,” Lisa said. “Time is your biggest asset, so use it accordingly.”

Attitude is important, too. If you approach a date like it’s something you want to get through as fast as possible, of course it won’t be fun.

Give your date your full attention on a dinner date, and you’ll give it the chance to actually result in a deep connection.

As for coffee dates, try to avoid them unless you’re not particularly excited about the date. “If you’re not too serious about it, they’re okay,” Lisa said. In most cases, though, you should be excited about anyone you’re going out with!

We wanted to know if kissing on the first date is still romantic and permissible in this post-MeToo dating world.

“Absolutely,” Lisa told us. “It’s a great way to end the date, to show that you like each other, that there’s affection.”

It can be hard to feel true chemistry on a first date, especially when it’s the first time you’ve met. If you do feel that chemistry, it’s special! Lean into it. 

A goodnight kiss offers the perfect amount of romance to leave you excited for the next date.

“Yes, yes, yes to kissing on the first date,” Lisa said.

According to Lisa, taking the physical a step further and going home together is a little more complicated. “Sleeping together, that’s a whole different story,” she said.

“You can do this, but it has to be for yourself,” Lisa said. “You cannot spend the night together, having big expectations of a relationship to come just because you did spend the night together.”

Sex for the sake of sex or because you felt a strong connection is perfectly fine. Just know it won’t make a person want to start a relationship with you, and sadly, it may complicate relationship prospects. 

Some people still struggle to see a relationship with someone they’ve hooked up with early on.

Men often say they’re worried about coming across as creepy or being accused of harassment for asking for a second date. Lisa says it’s not creepy to be direct and show interest.

Women will almost never be offended by saying you’d like to go out another time. “It’s as simple as leaving the date saying, ‘I’ve had a great time, and I would love to see you again,’” Lisa told us.

Try to be intentional about when you bring up a second date. “Timing matters here, too,” Lisa explained. “If you decide you want to see her again during the date, set a date for the following weekend and let her know that you’re really interested in seeing her again.” 

“There is nothing creepy about being confident, direct, and knowing what you want.” — Lisa

That can make the dreaded “When can I see you again?” conversation feel more natural. It also saves you the suspense of reaching out after the first date.

What can be creepy is too much persistence. If a woman tells you she isn’t interested – or even hedges, saying something like “I’m not sure” — let it go without argument.

It may feel like dating in 2025 is a world away from how it was for our parents, grandparents, even our older siblings. And while the standards for dating may truly be a bit higher nowadays, many of them come down to just being kind.

But, when in doubt, these three rules will help you master dating etiquette for 2025, and hopefully, a few more years after that!

1. Date with Intent

“People are done wasting time in 2025,” Lisa told us. “They’re done on the apps and dating to be dating.”

Instead, singles are considering what they truly want out of dating and a relationship.

Young singles in particular are being more intentional in how they pursue new romances and set expectations that align with the future they desire.

“Think about that when considering your next Friday night,” Lisa said.

2. Communicate Clearly

“We really want openness and directness,” Lisa said. This applies to dating logistics, like whether you want to keep seeing someone, but it also applies to bigger topics, like values and life goals. 

Do you want kids? How’s your relationship with your family? When do you see yourself getting married?

“No matter what the topic, just be ready to talk about it,” Lisa advised.

3. Be Emotionally Available

“I know that’s kind of tough,” Lisa said, “but it’s very attractive and sexy to be emotionally available and vulnerable in certain situations.”

“Emotional availability” is a term that gets thrown around a lot, and you may be unsure what that means. Not everyone is super emotional, and that’s fine. Emotional availability simply means being willing to share what you are feeling with your partner instead of shutting them out.

No one goes into dating with a perfect understanding of how to be thoughtful, attractive, and discerning. We all need other people to help us date well. 

For some people, that means relying on friends and family. But they aren’t experts.

If you’re looking for guidance throughout the dating process — what to wear, what to ask, maybe even who to date — Lisa’s team at Selective Search Luxury Matchmaking has the answers.

Not only can they set you up on truly compatible dates, they can help you find clarity about what you want out of dating and how to show up for your dates.