22 Second Date Rules to Guarantee You Get a Third

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Congrats! You’ve made it to that second date. Now’s a great opportunity to really get to know this guy and see if there’s long-term potential.

But you’re still in murky waters. Going out twice with a man doesn’t necessarily guarantee that you’ll end up in a relationship…or even that you’ll go on a third date.

Why The Second Date is So Important

First dates are basic Dating 101; you’re just seeing if you are potentially interested in one another. But sometimes you can’t really get a sense of whether or not you’re a good fit for each other in that first short date. You (or he) might be nervous. You might have trouble engaging in conversation. You might be so worried about whether you have spinach between your teeth that you can’t really relax and have a good time.

But on a second date, you’re more relaxed and ready to dive deeper. You’ve likely chatted with this man since the first date, either via text or on the phone, so you’re a little more comfortable and have more to discuss on your date.

And the fact is: 61% of single men and 70% of single women are more excited about a second date than a first, so you’ve got the potential to have a lot more fun this time!

Tips To Rock That Second Date

Relax. You’ve got this. Your second date will be the best!

Now that you know how important a second date is, you might be understandably a little nervous. What if you screw it up? How can you figure out whether he’s boyfriend material or not?

Not to worry, Sexy Confident lady. I’ve got proven tips to help you have the best (and maybe last) second date ever.

Editor’s note: Ready to attract love with a proven strategy? Watch this free video to learn the 7 powerful steps

1. Choose a Quiet Venue So You Can Talk

Most people put the most effort into choosing an impressive venue for the first date, but where you have your second date is just as important. And because you want to focus on getting to know one another, you’re better off choosing a quiet place so you can talk.

That means: skip the indoor concert. Have a picnic in the park. Say no to a crowded bar. Say yes to a quiet restaurant. My point here is that the venue for your second date shouldn’t compete for your attention. You want to focus solely on this guy, talking and flirting with him, so you don’t need to have to shout over the noise to do it.

2. Kiss Him on the Cheek When You Meet Him

Especially if you didn’t have your first kiss on your first date, if you’re into this guy, you want to communicate that physically right away. A kiss on the cheek when you go to hug him is completely innocent, and yet communicates your interest…and maybe hope that the kiss will develop into something a bit more substantial at night’s end.

At the end of the date, if he hasn’t made a move to kiss you (and you’re not comfortable making that move yourself), give him another kiss on the cheek. This time, linger a little. Pull away slowly and see if he gets the message that you want to lock lips.

3. Consider Letting Him Pick You Up

While I encourage you to meet a man at the venue for a first date, for the second one, you might decide he’s trustworthy enough to pick you up. Still exercise caution, though. You don’t have to let him in when he picks you up; just walk out the door or be waiting for him outside (though if you wait inside, you can see whether he’s the kind of guy to walk up and ring your bell or to text you that he’s here. Very telling about the kind of person he is!).

Just as a safety tip: let a friend know where you’re going, and give her the man’s contact information. You can never be too careful.

4. Open Up More

Let him get to know more of your personality this time.

On the first date, you ran through your list of topics: family, music, food, travel, work. Now it’s time to go deeper. If this man is relationship material, you’ll need to know that you can connect on things that are important to you.

If you’re really into reading, ask what he likes to read. If you hate your job and are looking to make a career move, open up about that. Essentially, find topics that let him get to know your authentic self and that open the door for him to share more of who he is.

5. Touch Him to Express Interest

Just like that sweet little kiss on the cheek, there are other ways you can physically show interest without going overboard.

When he says something funny, lean forward and touch him lightly on the arm while you laugh. If you tease him about something, touch him on the shoulder. Cross your legs in his direction. These are all ways you can let him know you’re having a great time through body language.

6. Tease Him a Little (But Don’t Make Fun!)

Some gentle ribbing on your second date can break the ice and get the both of you laughing, but keep it kind. The last thing you want to do is make him think you’re a mean girl!

Maybe you both show up wearing plaid that night. You could say, “I got the memo that we should both wear plaid. Dates are more fun when we coordinate!”

If there’s the possibility that what you want to say could hurt his feelings, don’t say it. You don’t yet know how sensitive he is.

7. Do Something Different Than You Did on the First Date

If you went to a bar on your first date, don’t go to another bar. If you walked on the beach, choose another activity. The early days of dating are as much about having different interesting experiences together as they are about getting to know one another, so find ways to mix it up.

If he suggested the spot for your first date, take initiative and plan the second one yourself.

8. Ask Some Dealbreaker Questions

Bringing up whether he has or wants kids, what his stance is on marriage, and what his political affiliation is on a second date might seem a bad idea. Depending on his answers, you might guarantee you don’t get a third date, but that’s a GOOD thing if you realize that you’re not compatible.

Let’s say you ask whether he wants kids or not. He says absolutely he does. But you in no way want any (or more) children. Would you rather find out now and end things or try to make things work, knowing that at some point, this issue is going to mean more heartbreak?

It’s better to get these big topics out in the open early so you can each go your separate ways if you aren’t aligned.

9. Pay Attention to His Body Language

Just like your body language is communicating something to him, so, too, is his telling you something. You just need to pay attention to see what it’s telling you.

If he’s leaning away or crossing his arms a lot, he may not be as into you as you hope. But if he’s leaning forward and touching you on the arm or back, he’s just as excited to be with you.

10. Offer to Pay

I realize that everyone’s got a different stance on who should pay for the date. Some say the man should always pay. Others say whoever planned the date should pay. I just think it’s good manners to offer to pay. He may not let you, but at least you’ve communicated that you’re perfectly willing to pay, and that you’re not looking for a man to take care of you.

11. Give Him a Second Chance

You might not have felt sparks fly on that first date, but that doesn’t mean he’s not right for you. In fact, 59% of single people said they don’t expect to feel chemistry until the second date, and about 30% don’t expect it until at least the third.

The two of you may need more time to be at ease around each other to really determine whether there’s chemistry or not. So even if you didn’t feel a love match on a first date, if he asks you out again, give him a chance.

12. Recall What He Told You on Date #1

Show you were paying attention!

This is such an easy way to impress a guy: just remember what he told you on the first date (or in your conversations). It shows that you’re paying attention, and that you’re invested in him enough to care.

You: “Hey, how did your mom’s knee surgery go?”

Him: “Wow, I can’t believe you even remembered that. It went well, thanks.”

13. Ask Thought-Provoking (+ Silly) Questions

Your second date should be a mix of deep and light topics. Try to avoid questions that have yes/no answers so that your date has to give some thought to his reply.

You could always play the Would You Rather game:

Would you rather never see again…or never hear again?

Would you rather never be able to eat your favorite food again but have millions of dollars…or be able to eat it but be dirt poor?

Would you rather be a bat or a snail?

If the conversation is getting heavy (maybe you accidentally wandered into Talking About Our Exes territory), veer toward one of these lighter questions to change the vibe.

14. DON’T Talk About Your Ex

Speaking of talking about your ex…don’t do it! I know that sometimes it can’t be helped. It’s natural to ask one another about the past. If he asks if you’ve ever been married and you are divorced, just give him the facts (“Yes. I got divorced three years ago.”) and move on.

Just don’t badmouth your ex or spend more than a few seconds on the subject.

And of course, if you’re telling a story about your past and your ex was part of the story, you can mention him…or just tell the story as if you were alone (“A few years ago, I was in Antarctica…”).

15. Flirt More

On your first date, you may have not been sure of whether you liked this man or not, so you probably didn’t do much flirting. But now you realize you’re into him, so it’s time to step up your flirt game.

Smile often. Engage with him by making eye contact. Find witty things to say. Actively listen to what he’s saying, and ask questions. Essentially, make him feel like the center of the universe on that second date!

16. Include Multiple Venues for Your Second Date

Extending the date to post-dinner dessert? Sweet!

There’s no rule that says you have to sit in one place for three hours on a second date! If dinner ends and you’re not ready to call it a night, suggest a stroll through the nearby park. Or maybe you get dessert or a nightcap at another spot.

Don’t be afraid to get creative! If he talks about how much he loves the marshmallowy candy, Peeps, grab his hand after dinner and say, “C’mon. We’re going on a Peeps scavenger hunt.” You can go to every drugstore within a five-mile radius to buy as many colored Peeps as you can find. That’s a memorable second date!

17. Make it Longer Than the First Date

While there’s no hard and fast rule about how long a first date should last, I often suggest a short-and-sweet coffee date, particularly if you’re meeting a man from a dating app. That gives you enough time to decide whether you want to get to know him further, while still being short enough that you can suffer through it if the date is abysmal.

But now that you’re headed out on a second date, you should spend more time with this man, now that you realize there’s potential there. Plan for a multi-venue date like in Tip #16, or pick something that will take a while. You could go on a long hike, visit an amusement park, or go to an outdoor festival.

18. Compliment Him

You might be thinking that he looks hot…but he doesn’t know that. Make sure to vocalize any compliments you’re thinking so that he can enjoy them. Who doesn’t love compliments?!

The key with compliments is to be sincere. People can smell a fake, overdone compliment a mile away. And mix them up: you can compliment him on how he looks or smells, but also later compliment something about his wit or intelligence.

Just don’t go overboard!

19. Lock Down Date #3

By the end of the second date, you should be pretty confident that you’re going to see this man again, but don’t end the date with a vague “let’s do this again soon.”

Make a plan for that third date. Maybe he mentioned that he’s never been to your favorite Russian restaurant. Suggest it, along with a day in the next week to go. Put it on your calendar!

20. Go in for the Kiss (If You Didn’t on Date 1)

The time to lock lips has come!

If you didn’t kiss this guy on your first date, now’s the time to seal the deal. You know you have conversational chemistry because you two talked until the server told you that the restaurant was closing.

But what about physical chemistry?

While not every first kiss is always the most magical, it can give you perspective on this guy and his potential. If you walk away from that kiss with butterflies in your stomach, that’s awesome. If you walk away wiping his spit off of your entire face…well…you might need to train him better on how to kiss.

21. Text Him Afterward

You’re not done with your effort after that second date. Reassure him that you had a great time by sending a text within an hour or two after the date thanking him.

I had such a good time tonight! Thanks for making wine shoot out of my nose with your crazy humor. Looking forward to Saturday!

Who knows? He might even respond right away, and the two of you could end up in one of those post-date texting marathons that lasts half the night. Just one of the perks of the early days of dating!

22. Relax! He Already Likes You

If, after a day or two, you start to get nervous about whether he really had a good time or whether he’ll call you…relax. You’ve made it this far. You paid attention to his body language, and it told you that he’s ready to take things to the next level.

Certainly this doesn’t guarantee that this man will be your next husband, but it does mean that you can let down your guard a little. The more comfortable you feel around this man, the more yourself you can be. And that will only make him want you more.


Enjoy yourself on that second date!

To me, a second date is even more fun than the first because there’s less anxiety and anticipation. If you’ve only talked online or via text before a first date, you have no idea how the two of you will be together in person. Sometimes you can have great text flow but be rotten at conversing face to face.

But by that second date, you already know that you dig this guy. So enjoy it! Don’t overthink what happens next.

Tell me and the rest of our Sexy Confidence community in the comments below what your best ever second date was. Did you go on a third?

What do you think? Share your thoughts below...

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3 years ago

Thank you so much!

3 years ago

Thank you for your tips!! I hope this will work this weekend. 🙂

2 years ago

Great tips! Thanks!

Kimly Sieng
2 years ago

Thank you for the tips Adam!

1 year ago

Very helpful. Thank you.

Karen H
6 hours ago

I am reading this after the second date. We connected even better on the second date. Kissed. He stated how glad he was to find a match in his town instead of long distance. We discussed getting together again but his response was “we’ll see”. I did most everything mentioned above. Let me explain a bit more, he helps out with his 92 year old mother who is still living in her own house. The day after our first date, his only brother died unexpectedly. I was patient and supportive, never pressuring him. I have dealt with the loss of… Read more »

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