15 First Date Tips to Help You Land the Second Date!

3 min read

Anthony O'neal
15 First Date Tips to Help You Land the Second Date!

We’ve all been there: You meet someone amazing online or while you were out, and you’re about to go on a first date together. If you want that first date to turn into a second and a third, then listen up. I’ll keep it real: I’ve been on a lot of first dates. I don’t know if that qualifies me to talk about dating, but I’m always willing to share what I’ve learned from my mistakes and successes. So, here are my top 15 first date tips that will almost guarantee you a second.

1. Choose the Right First Date Spot. 

Avoid places that are too loud, like night clubs or busy bars, and steer clear of places that are too quiet, like movie theaters. Instead, do something casual and low-key with potential to level up if things are going well. Think going to a coffee shop together or grabbing a drink somewhere chill with a nice vibe. These are great options because they’re low-pressure environments that give you a chance to get the conversation going. Then you can move on to dinner if you’re enjoying yourselves.

2. Take Safety Precautions.

If you’re meeting someone in-person for the first time, make sure you’re being as safe as possible. Have your first date somewhere public—don’t go to each other’s houses. And unless you know the person well, I recommend meeting each other at the date spot instead of picking each other up at your homes. I also suggest telling someone where you’re going ahead of time. Sharing your location with a trusted friend or family member isn’t such a bad idea either. When you both feel safe, you can relax and enjoy the date more.

3. Don’t Put a Ton of Pressure on the Date. 

It’s normal to feel nervous or anxious before the date, but just breathe and relax. Remember: The first date is to decide if you want to go on a second date not if you want to marry them. Some of us feel pressure to get into relationships or get married, and we take that into our first dates. But your date can tell when you’re desperate, and it might scare them off. So take the pressure off of yourself, take the pressure off of them, and go on your date with an open mind. If you click, cool. If not, no worries. There are plenty of other great men and young ladies that you can click with.

4. Dress Nice, but Be Comfortable. 

You want to make a good first impression — and that starts with your looks. Guys, don’t show up in a pair of sweats and a wrinkled shirt. Invest in a good pair of jeans and a nice dress shirt. And dress for the date you’re going on. Ladies, you don’t have to wear high heels and a dress just because it’s the first date. If he’s taking you to coffee, wear something comfortable and more casual. Trust me, you’ll still look amazing. 

5. Ask Good Questions. 

The whole point of the first date is to get to know each other and see if you’re a good match. Thinking of interesting questions ahead of time is a good way to learn more about them and show them that you’re interested. But don’t make it feel like an interrogation or a job interview. Listen to their responses, engage in the conversation and let them ask questions too.

Here are some good questions to ask on your first date:

  • What’s your last name? (For my online daters)
  • What’s something you learned during the COVID-19 pandemic?
  • Where have you traveled?
  • Among your friends, what are you best known for?
  • What are some accomplishments that you are really proud of?
  • Do you attend church?
  • What do you want your financial future to look like in 10 years?
  • What’s the best and worst advice someone has given you?
  • Where would you move if you could move anywhere in the world?

6. Compliment Them (but Not Too Much).

Everyone likes a genuine compliment, but too many compliments make people uncomfortable. If they show up looking like Beyoncé or Michael B. Jordan, by all means, give them a genuine compliment on their appearance. “You look beautiful,” or “You look amazing,” are good lines, but don’t overdo it. 

If you’re the type to give out lots of compliments, compliment something other than their looks, like their laugh, sense of humor, intelligence or ability to ask good questions. It’ll tell the other person that you notice things about them other than their appearance.

7. Have a Dating Budget and Stick to It. 

Forreal, you don’t need to spend a lot of money on a date. When I make my monthly budget, I’m sure to include a category for dating, and I make sure I stick to it. Fellas, I suggest you do the same. Ladies, you too, just in case he takes you out and doesn’t pay. 

I’ve gotten some flak for sticking to my budget in the past, but sticking to a budget doesn’t make you cheap—it makes you a good steward of your money. And that sounds like marriage material to me.

8. Stay Cool and Be Yourself. 

A lot of people feel critical of themselves, especially before a date, but there’s nothing more attractive than a person that’s confident and comfortable with themselves. It’s normal to feel nervous or anxious before a date, but don’t let it psych you out. Talk about your actual hobbies, make a joke or two (nothing raunchy or sexual, though) and be confident when you respond to their questions. Don’t make up stories or stretch the truth.

If you’re nervous about whether they’ll like you or not, remember that they agreed to go on the date because they’re interested in getting to know you too, so don’t overthink their feelings for you. 

If you’re your authentic self from the start, your date will fall in love with the real you, not this fake version of yourself. And your future dates will go a lot smoother.

9. Be Flexible. 

This is for all of my super detailed, type A personalities out there. While you’re on your first date, leave room to be spontaneous. For example, you get to the restaurant and the hostess can’t find your reservation. Don’t freak out. Stay cool, apologize to your date for the mixup and find a new spot to go eat. It shows that you can stay calm in stressful situations, think of your feet and go with the flow.

10. Pay Attention to Red Flags. 

It’s easy to miss negative things about your date while you’re having fun and getting caught up in the moment, but don’t get too carried away. They might be flashing some red flags that you need to pay attention to. Some red flags you might see on a first date are: 

  • They’re very confrontational.
  • They don’t ask questions about you.
  • They’re rude to the waiter.
  • They pressure you to do and try things even after you said you don’t want to.
  • They make fun of your interests, beliefs or ideas.
  • They make sexual jokes.

11. Have Difficult Conversations. 

Of course, you want the first date to be fun, but don’t be afraid to talk about difficult topics if they naturally come up in conversation. Remember: You want to make sure this person is compatible with you. Religion, politics and money are all important parts of that, so don’t be afraid to discuss it. Just remember to speak respectfully and listen to your date’s opinions too. 

I’ll give you an example: I’m a man of God, so I’m always bringing up my faith no matter who I’m with. If my date isn’t Christian, it’s better I know that on the front end so she and I don’t waste each other’s time. Identify your deal breakers and don’t be scared to part ways if y’all aren’t a match.

12. Pay Attention to Your Body Language. 

Your body language speaks just as loudly as your words, so watch your posture while you’re on your first date. When your date is talking, lean forward, make eye contact (but don’t overdo it) and nod your head to show you’re listening. Avoid crossing your arms, looking distant or breaking eye contact for a long time. Doing that will make your date uncomfortable and send the message that you’re not interested. 

Also, put your phone away during your date! Put it on silent and keep it out of sight. Constantly checking your phone tells your date that you’re not fully engaged or listening. So, ditch the cell phone and be present.

13. Avoid Too Much Cussing and Dirty Jokes. 

Don’t try to talk like someone else on your date; Be yourself. But, too much cussing and crude jokes on your first date might offend or scare your date off. So, keep it clean. 

Also, avoid speaking negatively about others, yourself or your life. It makes you look like a negative person without much self worth. Instead, talk about the things you enjoy, people you care about and aspects of life that light you up inside. It’ll make you even more attractive to your date.

14. Send a Follow-up Text, or Call Them. 

After your first date, call or text the person to check in on them. Don’t wait days and weeks to do this, especially my brothas out there. If you like a girl, you have to pursue her, and that means reaching out after the date to make sure she made it home and see if she had a good time. Ladies, you can follow up, too. A text message letting them know you made it home and that you had a good time (if you did) is enough. But be honest. Fellas, if you weren’t feeling it, then don’t ask her to go on a second date, and ladies don’t just say yes. Respectfully decline and wish them well.

15. Reflect on Your Takeaways. 

Reflection is important after the first date. It’ll help you decide whether you want to go on a second date with this person or not, which is what this is all about.

Ask yourself these questions:

  • What went well?
  • What would I do differently next time? 
  • What qualities did this person have that I admired? 
  • Did anything happen that felt weird or off?

I hope these lead you to a successful relationship and a better understanding of yourself.

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