What to Expect on a First Date

Published On: May 16, 2024|Categories: Advice for Men, Dating After Divorce, Dating Over 50, Dating Tips, First Dates|9 min read|

Dating today can feel like walking through a maze blindfolded. Especially if it’s been a while since your last great first date, putting yourself out there can be scary. Many of our clients begin their matchmaking journey without a good idea of what to expect on a first date, let alone how to navigate pre- and post-date communication.

All the advice says to be yourself, be confident, and the rest will fall into place. But what if you’re nervous, and the version you’ve presented isn’t getting second dates?

Don’t worry, we’ve got you covered! This is your guide for what to expect on a first date in 2024.

What’s Changed About Dating?

Some things about dating will never change. The end goal is still to find a compatible partner who you want to pursue a relationship with. Beyond that though, the landscape has surely evolved since the last time you were looking for love.

Here are a few things that might have affected the dating landscape since your last first date:


Texting your date before your first meeting has become the norm. While every person’s texting preferences are different, in general exchanging a few messages in the time leading up to your date is the accepted way to do things.

Texting the day of your date to confirm plans is both accepted and appreciated. This gives you both a chance to smooth out any last-minute miscommunications and to ensure that you’re both on the same page. It also lets your date know you’re excited to meet them!

Online Searches

It’s also become increasingly common to do a little digging online to find out more about your date. Many singles look their dates’ names up online or seek out their social media profiles to look for more information.

While we understand why many singles feel this is necessary, we don’t recommend this relationship reconnaissance. Part of the fun of dating is learning about one another slowly, and that can’t happen if people have already formed judgments about one another based on what they’ve found online.

Relationship Goals

Dating goals have changed from the days when marriage was the intended outcome for a dating relationship. Casual dating and hook-up culture have become more prevalent, and fewer people are adhering strictly to traditional ideas of courtship and marriage. Even among those looking for a serious relationship, getting married often isn’t a top priority.

Changes in demographics, such as an aging population and a higher divorce rate, have altered the dating pool. Women are more empowered to pursue careers, leading many to pursue marriage later than their grandmothers. More single adults are also re-entering the dating scene later in life.

For many, marriage isn’t the right choice, but that doesn’t mean another kind of commitment isn’t possible.

Gender Roles

There’s been a shift in gender roles within dating. While traditional dating etiquette is still generally accepted, many singles today are looking for a more egalitarian partnership. Things like splitting the bill on a date might have once been taboo, but today are quite common.

Our matchmaking team has seen countless clients work through first date jitters, and they’re experts at guiding them through the process. Read on to learn their advice for planning a great first date and seeing it go off without a hitch.

Planning a First Date

A first date is just an introduction. Although a lot has changed, the basics are still the same. It’s likely you’re both feeling some butterflies, and that’s okay.

Expect for you or the other person to be nervous. That part still has not changed. Know that it is still expected to be a gentleman or lady. I feel even though there are lots of shifts in our society that part of things is still much appreciated and expected.
Janel, Matchmaker

One thing that we hear often from clients is that they struggle to plan an interesting date. Instead of always trying to find a perfect compromise, Rosalind has heard a great solution.

“If they’re pursuing anything past the first date, I’ve heard from clients that they plan one date with what they want to do in mind and then switch it up the next time around.”
Rosalind, Matchmaker

But what do you do before you make it to the second date? Planning an activity for a virtual stranger can seem like a daunting task, but with a few basic guidelines, it becomes a breeze. The ideal first date location is a place that fits the following criteria:

  • An activity that naturally concludes after an hour or two. This could be something like coffee or a casual meal.
  • A place that’s relatively quiet, but where conversation is still welcome. This is why a movie is NOT a good choice for a first date.
  • A public place that’s well-populated and easy to get to for both of you. A local shopping or main street district is a good place to start looking. There will be plenty of time for home visits, secluded areas, and road trips after you’ve gotten to know one another a little better.

We recommend our clients have a casual meet and greet for the 1st date, maybe coffee or lunch. This is just to get to know the basics about each other and to see if there is a connection enough to go on a 2nd date. Then, get to know each other slowly using the 3 Date Rule.
Megan, Senior Matchmaker

Modern Dating Etiquette

There are some things you can do to give the date its best chance of going smoothly. First and foremost, there are certain topics our team recommends stay off the table for the first couple of dates. Some of these include traumatic experiences, past relationships, financial struggles, and medical issues.

Even though your past relationship played a big role in your life, that is the past and everyone here is to move forward, so don’t dwell on past relationships.
LeighAnn, Matchmaker

Of course, it’s always up to you what you’d like to disclose about yourself. We have found, however, that talking about intimate or personal topics such as these can make the receiving party uncomfortable. This can hurt your chances of forming a connection, regardless of your overall compatibility.

  • Matchmaker LeighAnn advises all her clients to wait at least until about the third date before bringing up heavier topics like politics and religion. “Get to know your introduction a little first before judging their opinions and beliefs,” she says.
  • Another thing our team agrees should stay out of your conversations early on? Past partners. “So many people talk about poor relationships they had, they tend to be very negative. I feel more clients need to be aware this is a hindrance to them,” says Megan, a senior matchmaker here at The Matchmaking Company.
  • If you do bring up your past relationships, try to keep it positive, and follow Lori’s advice. “bring the conversation back to yourself. So you could say, ‘When my spouse and I went to this vacation spot, I like to do this, I looked forward to seeing the museum.’ This allows you to share, but it still keeps the conversation focused on you, not your past relationship.”
  • To keep their conversations positive and engaging, Rosalind recommends her clients learn three fun facts about one another. “I recommend this to encourage equal conversation, so one voice doesn’t accidentally dominate the first meeting,” she says.

Most advice isn’t gender-specific. However, men and women do have a sort of ritual to follow when it comes to dating one another. Our team has some more specific pointers for those who are looking to make a gentlemanly or ladylike impression.

“So many clients are lost when it comes to dating from being in one relationship for so long. Men tend to struggle with asking questions, while women sometimes don’t realize it is not okay to ask emotionally intimate questions of a total stranger. Across the board, both men and women have a hard time keeping things light. When you haven’t dated, it’s hard to remember to be engaging on a surface level to start. ”
Lori, Matchmaker and Coach

Advice for Men

When it comes to first dates, our team has seen it all. While first date blunders can happen to anyone, these are the areas we’ve noticed men struggling most often.

  • Ask questions. Nervousness can make a rambler out of even the best conversationalist. Make sure you’re taking time to listen to your date as well. She’ll appreciate having your full attention.
  • Take a shower beforehand. This shows that you take pride in your appearance. It will reassure your date that if you go to a nice place together, she can confidently walk in on your arm.
  • Make sure your outfit is nice. While appearance isn’t everything, it’s a big part of making a good impression. Choosing a flattering outfit for your date shows that you care about what she thinks and you want to impress.

For a lot of my clients good etiquette has a lot to do if one or the other shows up clean cut and well dressed for the environment they chose to meet.
Janel, Matchmaker

Advice for Women

Once again, while these things aren’t exclusive to women, our team has observed that ladies tend to struggle more often with the following things:

  • Don’t be afraid to make the first move. It’s not the way you might be used to, but it’s the 21st century! Men want to be pursued, too, and the initiative is likely to be seen as attractive.
  • Although the temptation to dig deep is understandable, stay away from intimate or intensely personal questions for now. Getting to know each other slowly is part of the fun of dating. As your connection grows, there will be time to discuss things like past relationships and finances.

As a woman, you can always reach out to men first or text more often, rather than letting them always reach out to you. Equal effort makes both parties feel safer sometimes.
Rosalind, Matchmaker

Final Thoughts

Dating today might look a little different than it did in the past, but fundamentally, it’s still the same. It’s just two people who are both nervous to meet each other, yet hoping to make a connection. While there’s no guaranteed formula for getting it right, Matchmaker Rosalind sums it up well:

“Pay attention to what first impression you’re making and what they’re making. Keep your cards close, but don’t be afraid to be honest about how you’re feeling. Talk about the anxieties you might have or any reservations. Polite honesty is the best policy, always.”
Rosalind, Matchmaker

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