Skip to Main Content

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

I’ll be honest: Your boy has been on a lot of first dates.

Now, I don’t know if that makes me more qualified or less qualified to give first date tips, but I feel like you guys can get some good information from the hours I’ve invested into dating, the mistakes I’ve made, and the things I’ve learned. So, here are my top 15 first date tips that will help you be calm, cool and collected (and confident!) on your next date.

1. Pick the right first date spot. 

When you’re trying to get to know someone, you don’t want to go somewhere too fancy or loud, or someplace where you aren’t able to have a conversation (like a movie). The point of the first date is to see how well you guys vibe with each other, so talking needs to be part of the deal.

chat

The Dr. John Delony Show helps people through real-life challenges. Listen now!

Your best bet is to do something casual and low-key that has the potential to level up if things are going well. Think sitting down at a coffee shop or grabbing a drink somewhere chill where you can get the conversation going, and then transitioning to dinner afterward if you decide you want to spend more time with each other.

2. Think about safety.

Especially in the online dating scene, safety is important for both guys and ladies. Meet in a public place where other people can see you, and let a friend know where you’re going to be—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.

And unless you already know the person you’re going on a date with really well, don’t let them pick you up or drop you off at your house until you’ve established trust. You don’t need some random person from the internet knowing where you live. I’m not trying to scare you guys—I just want you to be safe out there!

3. Dress well. 

Wear something you’re comfortable in, for sure, but you should still put some time and effort into looking nice. Think about the atmosphere and dress code of your date location too—ladies, no need to wear those Louboutin heels to a coffee date at Starbucks. Y’all look good without even trying anyway. And dudes, get out of those sweatpants and put on some nice jeans and a non-wrinkled shirt (and add a blazer if you really want to look fly).

4. Don’t put a ton of pressure on the date. 

I get it, you guys. Maybe on the inside you feel desperate because you’re still single and don’t want to be, or maybe you’ve had a huge crush on this person for a while and really want it to work out. But just take a deep breath and relax for a minute.

The purpose of a first date isn’t to decide if you want to marry this person—it’s to decide if you want to go on a second date. Try to have fun and just enjoy getting to know them. If you click, that’s awesome, and if not, don’t force it. It’s not the end of the world.

5. Compliment them (but don’t overdo it). 

Both guys and girls really appreciate a solid, genuine compliment. If you give too many throughout the date, though, it can start to feel kind of cringey. A nice “Hey, you look great” is totally appropriate, but 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. 

Come up with some interesting questions ahead of time so you’re not drawing a blank and struggling to think of something while you’re sitting across from someone you’re attracted to.

In addition to the usual get-to-know-you questions, here are some ideas for what to ask:

  • 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 really thankful for right now?
  • What would your ideal day look like?

Don’t forget to listen intentionally to their answers, and don’t ask so many questions that it feels like a job interview or interrogation. Keep it fun and just be curious about the other person.

7. Have a dating budget. 

You guys aren’t going to believe this, but I’ve talked to some people who think that if you spend less than $500 on a first date, you’re cheap. What?

It’s okay to spend money on a date, but you should definitely have a reasonable amount set aside for it in your budget. Just like with every category of my budget, I’m disciplined about not going over my set amount, and I’ve gotten plenty of flak from ladies before when I wouldn’t go over that amount for a date. But hey, being able to stick to a budget doesn’t make you cheap—it makes you a good steward of your money, which is especially challenging as a single person. And that sounds like marriage material to me.

8. Watch your body language. 

Things like leaning forward, making eye contact, and smiling give off the vibe that you’re confident and engaged in the conversation. On the flip side, crossing your arms, looking around the room, and other things that make you seem bored or nervous are going to send the message that you don’t really want to be there.

Along with that, it sucks to be on a date with someone who’s staring at their phone or constantly checking messages. Put your phone away in your pocket or bag and challenge yourself to not look at it unless you absolutely have to—I promise, your date will be impressed and feel seen and heard because of how you’re choosing to be present with them.

9. Watch your language, in general. 

I’m not even talking about cuss words (even though you don’t need to be dropping those left and right on your date, either). I’m talking about speaking negatively or critically about other people, yourself or your own life—because complaining and criticizing says a lot about your own character and sense of self-worth. You don’t have to be fake, but you should focus on building others up with your words and keeping a positive attitude.

10. Look out for red flags. 

When you’re starting to like someone, it can be hard to notice red flags. But that doesn’t mean they’re not there, you guys. And right now, in the early stages, is the best time to notice them so you can decide what to do with them. Red flags could be anything as subtle as interrupting you one too many times during your conversation, or as huge as violating your physical or emotional boundaries. No matter what, make sure you’re doing everything you can to keep yourself safe. You don’t have to tolerate any foolishness, okay?

11. Go with the flow. 

You might’ve planned out every single detail of an incredible, romantic date like a baller—but don’t forget to leave some room to be spontaneous. You guys might decide that you really feel like getting ice cream instead of going to the art museum, and that’s totally cool. It’s important to be with someone who’s laid-back enough to not freak out when the plan changes!

12. Don’t avoid difficult topics. 

Ideally, first date conversations should be pretty fun and low-pressure. But if hard topics do come up, don’t feel like you have to change the subject. You want to get to know this person and see if you’re compatible, and sometimes the best way to do that is to talk about trickier topics like politics, faith, family history and stuff like that.

For example, I’m a man of God, so I’m always bringing up my faith no matter who I’m with. And if my date has an issue with that, it’s better to know that on the front end so we don’t waste each other’s time by continuing to date when there’s a clear deal breaker.

13. Don’t be afraid to be yourself. 

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

Remember that you have a lot to bring to the table, and choosing someone to date is just as much your choice as it is theirs. Going in with this mindset will affect how you carry yourself.

The truth is, you’re not for everybody, and not everyone is for you. In fact, not everyone should like you, if you’re truly being yourself. So don’t try to be something you’re not for some random person, no matter how hot they are.

14. Follow up afterward. 

It’s always polite to check in after the 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 and clear. If you really weren’t feeling it, don’t ask for or agree to a second date—respectfully, of course. But if you felt like there was some potential there, keep moving forward! Don’t make the other person wait forever to go out again if you know you want to.

15. Reflect on your takeaways. 

Whether you decide to go on a second date or not, take some time to think about what you learned from the date. What went well, and what would you do differently next time? What qualities did this person have that you admired? Did anything happen that felt weird or off to you?

All of these are super important questions to ask on your dating journey, and it’s my hope for you that all of this will lead to successful relationships—and an even better understanding of yourself.

For more tips and honest conversations about money, relationships and real life, check out my show, The Table with Anthony ONeal, on YouTube or wherever you listen to podcasts!

Anthony ONeal

About the author

Anthony ONeal

Anthony ONeal is a #1 national bestselling author, financial expert and host of the popular online series “The Table” on his YouTube channel. He has appeared on Good Morning America, the Tamron Hall Show, the Tom Joyner Morning Show and the Rachael Ray Show, among others. Since 2015, Anthony has served at Ramsey Solutions, where he teaches young adults how to budget, live without debt, avoid student loans and build real wealth for their future. Learn More.

Related Articles

8 Money Tips for Singles

8 Money Tips for Singles

8 Minute Read | Budgeting

Are you single and ready to . . . budget? Check out these eight money tips for singles that will help set you up for success!

Anthony ONeal Anthony ONeal

Deleting app to enjoy the single life

Can You Be Single and Happy?

7 Minute Read | Relationships

Listen, we all know being single ain't easy. If you’re struggling to see any good at all in the situation, here are some tips for dealing with the single life.

Anthony ONeal Anthony ONeal

Toxic Relationships

10 Signs You're in a Toxic Relationship

12 Minute Read | Relationships

A toxic relationship is one that drains, damages and exhausts you. Here are the common signs to watch out for.

Dr. John Delony Dr. John Delony