15 First Date Tips (to Help You Get a Second Date!)

Over the last decade, we’ve seen an explosion of dating apps and social media tools and sweeping changes in how people meet (both virtually and in-person), learn about each other, and ultimately end up sitting across from each other on a real-life date.

But it doesn’t matter how things change in the dating or technology world. People are people. We all need to have fun, explore new people and ideas, and have adventures. And the whole purpose of first dates is to connect, learn about people, and hopefully have fun, right? So let’s get at it—I’m sharing my best advice for a great first date.

15 Tips for a Great First Date

Whether you’re diving headfirst into the dating pool again or you’re dipping your toes in the water for the first time, there are countless ways to connect and have a great time on a first date. Read on for 15 first date tips that will help you feel calm and confident—and give you the best chance for a second date.

1. Pick the right first date spot.

When you’re planning a first date, don’t go somewhere too fancy or too loud. Pick somewhere lighthearted and relaxed. You want to hear and experience the other person. The point of a first date is to see how well you connect with each other—not how much you spend on dinner or how good you read lips over drum solos.

Think sitting down at a coffee shop, grabbing some cheap tacos, or going for a walk so you can strike up a conversation. If you and your date are hitting it off, suggest getting together later in the week to grab some dinner, watch a game, or check out a local songwriter’s night.

2. Be safe when you date.

When you’re dating, safety needs to be your number one priority—full stop. Especially in the online dating scene. I don’t mean to scare you, but when you agree to meet a stranger (from the internet!), you need to be smart and alert. To be safe on a first date, meet in a public place where other people can see you. Tell a friend where you’re going and when you expect to be home. You could even share your location with them so they can check in and see where you are if they haven’t heard from you by a certain time.

Unless you already know the person you’re going on a date with well, don’t share personal information, like your home or work address. I repeat: Do not share your home address! Once you establish trust, you can do date pickups and drop-offs at home. But in the early days, a stranger doesn’t need to know where you live.

3. Wear what feels (and looks) good.

Okay, let’s lighten the mood by answering a really important question: What should you wear on a first date? I’m not a big fashion guy, but I do know this: You can’t go wrong being comfortable and wearing something that helps you feel good about yourself.

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Please don’t wreck your budget or your comfort zone trying to impress someone you don’t know. Keep it simple but push back on the slacker vibe. Be respectful of both yourself and your date. Wash your clothes. Make sure they’re not a wrinkled mess. Be yourself but also know where you’re going (don’t wear a t-shirt to a nice restaurant or heels to go hiking).

4. Relax.

If you’re nervous about your date, take in a deep breath, hold it for three seconds, and let it out. Relax. The point of a first date isn’t to decide if this person is “the one.” Or to wonder if this is the last first date you’ll ever have. Or to imagine dying all alone surrounded by hundreds of houseplants and Arrested Development reruns on TV if it doesn’t work out. (You won’t.) You’re not weak, and you’re not crazy for having a heart that wants to love and be loved.

You’re here to find connection, share some laughs, learn about someone new, and eat nachos. But if you don’t click, don’t force it. As Taylor Swift instructs, “Shake it off” and move on.

5. Give thoughtful compliments.

Everyone appreciates thoughtful compliments if they’re given the right way. Telling your date, “Wow, you look great,” when you first meet is excellent. Creepily eyeing them up and down while you say it isn’t cool. So have balance and be respectful.  

The more you appreciate your date’s unique taste, the better. “Oh wow, your tattoos are rad! What do they mean?” “I love your sweater/shoes/hat.” People love to be noticed for things they care about. But giving too many compliments throughout the date can be overwhelming and off-putting. So, if you’re worried about coming on too strong, compliment your date on something other than their appearance—like their laugh, sense of humor, intelligence or great taste in music.

6. Ask good questions.

Before your date, come up with a few questions ahead of time. Actually think through some things you’d like to learn about your date. Instead of the usual get-to-know-you questions (do you really want to explain why Social Distortion is the greatest band of all time again?), here are some creative ideas that will help you get to know your date on a deeper level:

• What’s the last book you read, and what did you think of it?
• What’s your favorite gift you’ve ever received?
• What’s something you’ve never tried but always wanted to?
• What’s your favorite memory with your family?
• What do you think about budgeting? (Wink, wink.)
• Do you have any crazy travel stories?
• What’s the best piece of advice you’ve ever gotten?
• What’s the worst piece of advice you’ve ever gotten?
• When you feel stressed, how do you relax?
• What are you thankful for right now?
• What would your ideal day look like?

When they answer, actually listen. Don’t just wait for your turn to speak. Plug in. Carefully consider questions they may ask in return. Don’t ask so many questions that it feels like a job interview or interrogation. Keep it fun and be curious about the other person. Instead of judging their answers, appreciate this person’s individuality.

7. Have a dating budget.

Most of the time, dates cost money. But that’s not a big deal if you set aside a monthly amount for dating in your budget. Just like every other category of your budget, you want to be disciplined about sticking within your boundaries. If your date gives you grief for sticking to your budget, that’s their hang-up, not yours. It might be an early sign they’re not for you.

Living on a budget doesn’t make you cheap—it makes you a good steward of your money, which can be challenging when living on your own. And no matter who’s paying for the date, someone who sticks to a budget sounds like outstanding relationship material. Plus, there are plenty of ways to save money on dates without missing out on fun.

8. Pay attention to your body language.

Most of our communication is nonverbal. Moves like leaning forward, making soft eye contact, and smiling are cues that you’re confident, open and engaged in the conversation. But crossing your arms, looking around the room, compulsively checking your phone, or fidgeting can make you seem bored or nervous and send a message that you don’t really want to be on the date.

One more first date tip: Put your phone away and challenge yourself to not look at it unless you absolutely have to. It’s not fun to be on a date with someone who’s staring at their phone or constantly checking messages, and it’s not respectful for you to do that either. If you have to check in on kids or work, let your date know when and why you’re checking. They’ll appreciate how present you are with them.

9. Use positive language. 

Watching your language is more than not swearing like a sailor. It means you don’t speak badly about other people, yourself and especially your ex-romantic partners. Complaining, criticizing and whining says a lot about your own mindset and sense of self-worth and can put a serious damper on your date. You don’t have to put on a fake happiness mask, but you should build others up with your words, be grateful, and keep a positive attitude.

10. Watch out for red flags.

Red flags are signals that someone probably won’t be compatible with your standards and values. The early stage of dating someone is the best time to pay close attention to red flags so you can decide how to move forward (and avoid a more serious relationship disaster down the road).

Red flags can be as subtle as interrupting you one too many times during your conversation. They can look like showing up late or being rude to the coffee shop wait staff. Or red flags can be as big as violating your physical or emotional boundaries. No matter what, make sure you’re doing everything you can to keep yourself safe. Please do not put up with anything that makes you feel unsafe or uncomfortable. You’re worth more than that.

11. Go with the flow.

You might’ve planned out every single detail of an incredible, romantic date—but don’t forget to leave some room to be spontaneous. You and your date might decide you’d rather get ice cream instead of going to the art museum, and that’s cool—it’s part of the exploration and the adventure. It’s important to be with someone who’s laid-back and flexible enough to roll with the punches if (and when) plans change.

12. Don’t avoid difficult or personal topics.

Ideally, first date conversations should be fun and low pressure. But if hard topics come up, go with it—don’t feel like you need to change the subject. You want to get to know this person on a deeper, more authentic level and see if you’re compatible. And sometimes the best way to do that is to talk about hot topics, like politics, faith, family history and other important parts of life.

For example, if you’re a person of faith, you might want to bring that up no matter who you’re on a date with. If they have an issue with your spirituality, it’s better to know that sooner than later so you don’t waste each other’s time. At the same time, don’t ever share something that you don’t feel comfortable talking about.  

13. Be yourself.

Going on a date with someone new can make you feel self-conscious. And that’s normal! A lot of people—especially those who tend to be anxious or self-critical—ask, Do they like me? But you should also ask yourself, Do I like them?

Remember—you have a lot to bring to the table, and choosing someone to date is as much your decision as it is theirs. The truth is, you’re not for everybody, and not everyone is for you. The right person will find your quirks and imperfections lovable, so there’s no need to shape-shift your way into a stranger’s approval. The sooner you and your date can be your authentic selves, the sooner you’ll be able to truly get to know each other.

14. Follow up after your date.

It’s good manners to check in after your first date and thank the other person for spending time with you and taking you out (or letting you take them out).

This is also the time to be honest if you weren’t feeling it. No—it’s never comfortable admitting you don’t see this moving forward (lighting your eyebrows on fire might sound better than breaking it off), but it’s respectful to be honest. Ghosting someone can be cruel. Always kindly and clearly communicate the truth, even if you do it in writing. On the other hand, if you feel like there’s potential, keep moving forward one date at a time. Why wait forever to go out again if you want to spend more time with them? Tell them what you think and how you feel with kindness and clarity.

15. Reflect on your experience.

Whether you go out a second time or not, take some time to think and journal about what you learned from spending time with your date. Talk to a close friend or two. Discuss what went well. What would you do differently next time? What qualities did you admire about this person? Did anything happen that felt weird or off to you?

These questions help you figure out what you like, what works, and what you’re looking for as you date. And I know your experiences—the good, the bad and the ones you’ll tell your grandkids—will lead to successful relationships and an even better understanding of yourself.

Connect Using First Date Conversation Starters

Dating can feel like a long, uncomfortable journey, but with the right attitude, it can be one of the most fun and educational phases of your life. You’ll learn what you like to do, the qualities you enjoy in other people, and how you can grow and develop in relationship with yourself and others.

For more ways to connect with someone on a first date (or with any other humans), check out my Questions for Humans Conversation Cards. They’re perfect for a first date. You’ll have fun answering thought-provoking questions that can improve your conversation and relationships . . . and might even lead to a second date!