What to Expect on a First Date
Let’s be honest—modern dating feels like an extreme sport. If you’ve ever stared at your phone, overanalyzing a text or debating whether to swipe left or right, you’re not alone. Dating apps, social media, and shifting relationship norms have changed the way we connect. If it’s been a while since your last great first date, getting back out there can feel daunting.
But don’t worry—you’re not walking into the unknown alone! Whether you’re dealing with first date jitters, post-divorce anxiety, or just looking for fresh date ideas, this guide has you covered. Our expert matchmakers have helped thousands of singles navigate today’s dating scene. Now, they’re sharing their best advice on:
- modern dating etiquette,
- finding the right location, and
- making sure your experience is fun, effortless, and (hopefully) successful.
What’s Changed About Dating?
While the end goal is still the same, the way we get there has evolved. If your last first date was years ago, you might be surprised by some of the new norms of modern dating.
1. Texting Before the Date: Yes, It’s Expected!
“Texting the day of your date to confirm plans is both accepted and appreciated. It gives you both a chance to smooth out any last-minute miscommunications. Plus, it lets them know you’re excited to meet them!” – Janel, Matchmaker
Once upon a time, showing up on time was enough. Today, pre-date texting is a must. A few casual messages beforehand can help you both feel comfortable and build anticipation.
2. Social Media Stalking Is Real—But Should You Do It?
“It’s become increasingly common to look up a date beforehand. But part of the fun of dating is learning about one another naturally. That can’t happen if people have already formed judgments based on social media.” – Megan, Senior Matchmaker
Let’s be real: Almost everyone Googles the person they’re going out with or scrolls through their Instagram before meeting up. But is it a good idea?
While a little curiosity is normal, digging too deep can create unnecessary assumptions. Part of the fun of dating is getting to know someone in person, not through old Facebook posts.
3. Relationship Goals Have Shifted
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.
4. Changing 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.
How to Plan a First Date That Sets You Up for Success
A first date should never feel like an awkward interview or a three-hour commitment with a total stranger. The key? Choose a first date location that allows easy conversation, keeps things light, and has a natural time limit.
“A first date is just an introduction. Expect for you or the other person to be nervous—that part still has not changed. Even though there are lots of shifts in our society, it is still expected to be a gentleman or lady.” – Janel, Matchmaker
Here’s what makes a great first date location:
✅ Time-sensitive – Keep it around 1-2 hours. You can always choose to hang out longer if it’s going well!
✅ Engaging but casual – Coffee shops, wine bars, or scenic walking areas are ideal. Movies? Too quiet. Fancy dinners? Too much pressure.
✅ Public & neutral – Choose a space that makes both of you feel comfortable. A local café or bookshop is better than a secluded setting with too many unknowns.
“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
Modern Dating Etiquette: First Date Do’s & Don’ts
Dating rules aren’t what they used to be. However, there are still some universal do’s and don’ts. Here are a few first date red flags to avoid. Keep reading for some green flags to help your chances, too.
🚫 First Date Blunders to Avoid:
❌ Oversharing – Keep the deep stuff (past relationships, financial struggles, medical issues) for later dates.
❌ Talking about exes – Even if your last relationship was a train wreck, they don’t need to hear about it on day one.
❌ Skipping the hygiene check – First impressions matter. Shower, dress well, and look like you put in effort.
“My best first date advice for women and men in the dating scene is to leave exes out of it. Even though your past relationship played a big role in your life, that is the past. Everyone here is to move forward, so don’t dwell on past relationships.”– LeighAnn, Matchmaker
✅ First Date Do’s That Boost Your Chances of a Second Date:
✔️ Ask thoughtful questions – Keep the conversation balanced. Having a few good conversation starters planned can make the evening go smoother.
✔️ Stay off your phone – Be present!
✔️ End on a positive note – A simple “I had a great time—let’s do this again!” makes all the difference.
“So many people talk about poor relationships they had. On a first date, this comes across very negative. I feel more clients need to be aware this is a hindrance to them.” – Megan, Senior Matchmaker
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
The 3 Date Rule: How to Keep Things Moving
So, you nailed your first date location, breezed through the first date conversation, and felt a spark. Now what?
Enter the 3 Date Rule—a modern approach to deciding whether someone is worth pursuing. Instead of writing someone off too quickly, give it at least three dates before making a judgment call.
Many singles rush to decide a relationship’s potential after one another just one time. Let’s explain why the 3 Date Rule actually works.
🗓️ Date 1: The “get to know you” phase. First impressions can be misleading due to dating anxiety. No deep conversations—just a pleasant time.
🗓️ Date 2: Building rapport. You get a better sense of personality and humor. More comfort, shared interests, and maybe a little flirtation.
🗓️ Date 3: The chemistry test. By this point, you’ll know if there’s a connection worth exploring. You can assess real compatibility—do you genuinely enjoy their company?
“Why should you follow the 3 Date Rule? Because chemistry isn’t always instant. So many clients give up too soon. The 3 Date Rule lets you see if the initial spark has potential.” – Megan, Senior Matchmaker
Final Thoughts
At the end of the day, dating is about connection, curiosity, and a little bit of luck. Will every first date be magical? Nope. Some will be awkward. Others will be forgettable. And occasionally, you’ll meet someone who just clicks.
“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. Polite honesty is the best policy, always.“– Rosalind, Matchmaker
So take a deep breath, enjoy the dating experience, and remember: the right person is out there, and they’re probably just as nervous about meeting you as you are about them!
