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

Modern dating. It’s not quite like the olden days when you would ask the cutie next door to the high school dance and then become an item. The dating scene has changed a lot with dating apps, social media and the chance of meeting your future Mr. or Mrs. at the grocery store (because reaching for the same bag of baby carrots is the perfect grocery aisle conversation starter).

But it doesn’t matter how many things change in the dating world. People are people. We’re all eager to connect and have some fun in life. And if a first date leads to either of those two things, well, that’s a pretty good deal.

So, whether you’re ready to dive headfirst into the dating pool after a long break or you’re dipping your toes into the water for the very first time, there are lots of 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, you don’t want to go somewhere too fancy or too loud or someplace you can’t have a conversation (like a movie). The point of a first date is to see how well you connect with each other, so talking and enjoying each other’s company are important here.

Your best bet in choosing a first date spot is to go somewhere lighthearted and relaxed. You don’t want to deal with the pressure of a formal restaurant or the chaos of an amusement park for your first meeting. Think sitting down at a coffee shop or grabbing a drink somewhere casual where you can get the conversation going. And if it feels like you and your date are hitting it off, you can take it up a notch by going to dinner that night or suggesting a meetup the next morning for a walk or smoothie date.

2. Date safely.

Safety should always be your priority—especially in the online dating scene. It’s so important for both guys and ladies to date with caution. We don’t want to scare you, but remember—you don’t really know the person you’re going out with. 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 what time 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.

And unless you already know the person you’re going on a date with really well, don’t share super personal information like your home or work address. We repeat: Do not share your address! Once you establish trust, you can let them pick you up or drop you off at your house. But in the early days, a stranger doesn’t need to know where you live.

3. Dress for confidence and comfort.

Okay, we’re going to lighten the mood a bit by answering a really important question: What should you wear on a first date? Well, choosing an outfit you feel comfortable in is always a good idea. But to make a good first impression, you should also put some time and effort into looking nice. Think about the atmosphere and dress code of your first date spot. Ladies, it might not be appropriate to wear those stiletto heels to a coffee date at Starbucks, but flats are always a classic. And gentlemen, swap your sweatpants for a nice pair of jeans and an ironed shirt (and add a blazer if you want to look really snazzy).

4. Relax on your date.

Does love feel like a battlefield? Maybe you feel lonely on the inside because you’re still single and don’t want to be, or maybe you have a huge crush on someone and really want it to turn into something more. Just take a deep breath and relax for a moment.


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Here’s a nugget of wisdom for you: 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. That’s it! So, try to have fun, and enjoy spending time with and getting to know another human. If you click, that’s great. And if you aren’t feeling it, don’t force it. It’s not the end of the world. The old saying is true . . . there are plenty of other fish in the sea.

5. Give thoughtful compliments.

Both guys and girls really appreciate a thoughtful compliment if it’s genuine. Telling your date, “Wow, you look great,” is totally appropriate. But giving too many compliments throughout the date, though, can be a little awkward. So, if you’re worried about coming on too strong, just 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 so you don’t struggle to think of a conversation starter while you’re sitting across from someone you’ve just met.

Instead of the usual get-to-know-you questions (do you really want to explain why blue is your favorite color 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 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.

It’s okay to spend money on a date, but you should set aside a monthly amount for it in your budget. Just like with every other category of your budget, you want to be disciplined about not going over your limit. And if your date gives you flak for sticking to your budget, that’s their hang-up, not yours.

The thing is, living on a budget doesn’t make you cheap—it makes you a good steward of your money, which can be challenging as a single person. And no matter who’s paying for the date, someone who sticks to a budget sounds like potential marriage material. Plus, there are plenty of ways to save money on dates without skimping on fun.

8. Watch your body language.

Simple signals like leaning forward, making eye contact, and smiling are cues that you’re confident, open and engaged in the conversation. On the other hand, crossing your arms, looking around the room, 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 in your pocket or bag 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. Your date will be impressed and feel seen and heard because of how present you are with them.

9. Use positive language. 

Paying attention to your language is so much more than not using cuss words. It’s all about not speaking negatively or critically about other people, yourself or your own life. Words are powerful and have an impact on people. Complaining and criticizing says a lot about your own mindset and sense of self-worth. (And moping around with an Eeyore attitude can put a serious damper on your date.) You don’t have to be fake on your date, but you should focus on building others up with your words, being grateful, and keeping a positive attitude.

10. Watch out for red flags.

Just because bulls like to charge headfirst into red flags doesn’t mean you should too. And when you like someone, it can be easy to overlook red flags and other warning signs that this person might not be a good fit. The early stage of getting to know your date is the best time to pay close attention to red flags so you can decide how you want to move forward (and avoid a dating disaster down the road).

Red flags can be as subtle as interrupting you one too many times during your conversation or as big 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 anything that makes you feel at risk or uncomfortable, okay?

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 that you really feel like getting ice cream instead of going to the art museum, and that’s perfectly okay—and part of the fun. 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 pretty fun and low pressure. But if hard topics do come up, don’t feel like you need 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 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.

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 themselves, Do they like me? But you should also be asking yourself, Do I like them?

Remember—you have a lot to bring to the table, and choosing someone to date is just 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 loveable, so there’s no need to pretend your way into approval from a stranger.

14. Follow up after your date.

It’s always polite 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 and clear if you really weren’t feeling it. It’s never comfortable admitting you don’t see this moving forward, but it’s the respectful thing to do. On the other hand, if you feel like there’s potential here, keep moving forward one date at a time. Why wait forever to go out again if you know you want to spend more time with them? Communicate what you think and how you feel with kindness and clarity.

15. Reflect on your takeaways.

Whether you decide to go out a second time or not, take some time to think about what you learned from this experience with your 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 we hope your experiences—the good, the bad and the entertaining—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 that 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 Dr. John Delony’s Questions for Humans. They’re perfect for a first date. You’ll have fun answering thought-provoking questions that can improve your conversation and relationship . . . and might even lead to a second date!

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Ramsey Solutions

About the author

Ramsey Solutions

Ramsey Solutions has been committed to helping people regain control of their money, build wealth, grow their leadership skills, and enhance their lives through personal development since 1992. Millions of people have used our financial advice through 22 books (including 12 national bestsellers) published by Ramsey Press, as well as two syndicated radio shows and 10 podcasts, which have over 17 million weekly listeners. Learn More.

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