8 Ways to Win the Second Date

By Leslie Termuhlen

So you’ve got that special first date coming up...

Clearly, you’re interested in this person because you’re here, reading this awesome article. I get it—sometimes you just feel pulled towards someone and really want to make it work. You go for a run to clear your head, shower and even shave. No, it’s not a typical Wednesday night, IT’S DATE NIGHT BABY! You found a great date spot on The Round for your first date and it’s gonna be lit.

Now all you need are keys to winning that second date. Doing all of these—or a combination of these at least—will help you on your way to date numero dos.

1. Ask deep questions

You totally don’t need to know your date's whole life story and all about every ex-girlfriend they’ve ever had. But, how many times have you dreaded making small talk with someone?

Pouring over the juicy (hah!) details about what you studied in college and what you do for work can be quite routine. The basics are important, but they’re also surface-level. We recommend going deep with someone about an idea you have, or something meaningful to you. It will help you get a better feel for your match's compatibility. Think of a few good questions that are out of the norm and you should be good to go.

2. Keep your phone off the table

Do you really want Instagram notifications popping up when you’re on a date? No? We thought so. Keep the phone in your pocket/purse and give your date your full attention. Your time is valuable and so is theirs, so don’t waste it by sitting on your phone.

There is no bigger turn off than feeling like there is something on someone’s phone that’s more important than you. You chose to be with this person, so give them the attention they deserve. We all know this, so just keep the darn phone away.

3. Make consistent eye contact

Solid eye contact shows you’re interested and also shows confidence, both of which are good signs. Listening with your eyes is important too - communication is shown with your eyes while you’re listening as much as it is when you’re speaking. It’s super simple, but this gesture goes a long way. Obviously, please don’t stare the whole time - eye contact about 70% of the time will do just fine... any more and it could get a bit awkward.

4. Talk about what means the most to your date

Again, don’t just make small talk, go deep and listen carefully. Find out what means the most to your date. Is it their family, childhood, or dog? Then talk about those things. You know what they say, people light up the most when they’re talking about what they love… and we all want to be lit right? (Ba-dum-tss) If you’re asking the questions about your date, you’ll get a better sense of how well you and your date connect and earn some extra points for listening.

5. Don’t talk about your past relationships

This is self-explanatory, right? The focus should be on your current date, not failures in the past. However, this conversation has a great time and place: 4th or 5th date over coffee when you’re more serious in the relationship. If you’re bringing up or asking about exes on the first date, you’re going to seem a bit out there. Wait until there’s a proper foundation before diving in.

6. Avoid politics and religion

Generally a good suggestion, however, play it by ear based on your date's sentiment around the topic. For me personally, I like to know where people stand on these topics, but I don’t like to get down and dirty in this type of conversation until I know a person better. Sometimes getting to know someone before you discover their belief system or how they vote is best. You might be different, but I think these topics can create superheated conversations and are perhaps better left to a later date.

7. Don’t act disinterested

Some swear by acting disinterested, that the other person will chase you if you pull away - this may not always be the wrong idea, but definitely not a great or respectful first-date move. How are they supposed to want to take you on a second date when you don’t even seem like you want to be on the first one? Save the games for some other time… or never.

8. Show interest in a second date

Don’t beg for date two, but definitely show your interest. It’s also helpful to make a second date plan while you’re still in person with each other. It can be easy for people to ghost once you leave the date and start texting. But if you have a plan in place, it’s unlikely for a ghosting situation to happen, which is exactly what we’re aiming for. With this said, it’s often hard for people to say “no” in person if they aren’t interested so make sure you’ve picked up on their body language and level of interest before going for it.

Here’s the thing—people are interested or they’re not. If you both vibe, you'll be well on your way a second date, don’t screw it up! Just Kidding (almost)!

So just be yourself and you shouldn’t have anything to worry about. Sit back, enjoy the experience, eat some good food and do your best to get to know your match–the rest will be history.


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