How to get a second date…

Trey Hamilton
7 min readFeb 21, 2021

Tips that I guarantee you will get a 2nd date!

1. Keep the conversation going

People love it when someone can hold their own be full of a scintillating back and forth! Replying with great fully thought-out questions and responding to what the other person said is a great way to gauge interest. When the person you’re with responds to questions half-heartedly the other person who initially asked a well-thought-out question feels like the conversation is one-sided and will slowly look forward to the date ending. If they say something about themselves and are vulnerable enough to give you an honest and genuine answer. Respond and add extra opinions and thoughts to what they said.

Example:

Them: “Yeah, I really like going ice skating by myself when hardly anyone’s in the ice rink it’s a time when I really get to think”

You: “That’s really cool, I could totally see how you could be in your own thoughts and be lost in the atmosphere of an empty rink”.

That right there is a thoughtful response and will easily keep the conversation going. Keep going with that mentality and watch the magic happen! If you want them to be interested in you and you’re looking for the real deal. Talk about some things that matter to you. Share with them things that get your heart racing and give you life!

They’ll either embrace that part of you and start to fall for the very fabric that lines your personality throughout. Or reject that part of you and immediately change the subject. Ask about them, what things do they really like? Watch their soul come alive when you’ve prompted them!

2. Be on time

Maybe I’m the weird one here. But I find it attractive when someone is on time. It shows excitement, respect, and attraction. Mutual respect builds attraction. Show up on time.

Being late shows you could really take it or leave it. Even if that’s not what you meant it’s subconsciously shown and already painting you in a bad light with them. These days people notice every small facet of dating. That also includes punctuality. This is one of the easiest things you can improve! Most people see someone who is on time as responsible and someone that has their shit together. We’re such a judgemental bunch. Don’t leave even the smallest detail free to judge on a first date!

I’m not crazy, I know sometimes there are situations that come out of nowhere. But for the most part, you can be on time if you really wanted to.

If Jeff Bezo said, show up at the local 7/11 by 8:00am sharp and I’ll give you a million bucks. You’d make sure you were there the day before, haha! Hell, I’d camp out at that 7/11 for the money! So you can show up on time, stop making excuses and show how much you want to be there. That alone can secure a 2nd date. If you are going to be late, send a text or better yet. Call them.

3. Throw in those compliments

“I hate compliments” — No one ever

Most people who say they hate compliments aren’t telling the whole story. They like compliments but only when it comes from a genuine place or when it comes from someone they know. The rest of us fickle wankers love a good compliment to stroke the ole’ ego. It’s how we’re wired. No one refuses to go on another date with the person who tells them how cool their outfit is or how much they really adore their view on life. But don’t lay it on too thick.

A mistake a lot of people fall into.

But say it when it’s appropriate and when you see the right moment to make one!

Example:

Him — “Yeah that’s why I like to go to the art club after work on Wednesdays. It makes me feel like I have more going for me than a 9–5. Ya know?

You — “I like that a lot. In the time we’ve been speaking you strike me as a person who’s comfortable expressing their feelings with art. I admire someone who can do things outside of work”

See! That right there is all it takes. Give a compliment when the opportunity easily lends itself. This means you gotta shut your mouth and listen. Men love being on the receiving end of a compliment cause often it’s society that has spent decades subtly brainwashing men that they gotta shower women with vain compliments about their looks just to get them to like you. So giving a man some compliments is a great way to get that 2nd date! Compliments to a male on a date give him the subtle guided confidence he might need in order to ask you out for a second date. It’s sending him a green light that he’d be silly enough not to see that he should, in fact, ask you out for a 2nd date.

4. Show you’re easy-going side.

No one likes someone who takes themselves too seriously.

People can spot an uptight and unrelaxed person a million miles away. It’s okay to be nervous and a little unsure but convince yourself that no matter what happens you’ll have a good time and it’ll all work out no matter the result. That enables you to show who you really are and sail into that easy-going you.

Some of the most charismatic actors you know get so much love and adoration when they attend talk shows and have interviews.

Look at that charm!

Why? Cause they’re themselves. It definitely helps to be ridiculously good-looking and have millions of people watch your movies. But they got there with that laid-back and easy-going charm. Being fun and easy-going is another great way to lube up the notion of having another date. Who doesn’t want to date the funny person who’s so easy to talk to and emanates such a natural personality? Don’t put pressure on your date asking about a potential future between you too or how many kids you want, what do you think about marriage, and all that stuff. Be patient all that stuff will come. For now, just get to know the basics of getting to know each other.

5. Women can offer to pay, too…

Yes, yes! I know you’re probably banging your fist on your laptop cursing my text demanding that a, “A woman should never pay for the first date”. In my experience and most of my male friends, they all expect and plan to pay. I actually wrote a separate article about that found here. But for the most part, don’t ever assume even if you’re pretty sure they’re gonna pay that they ever will. When a man already goes there with the notion already implanted in his head to pay, when the woman offers. It’s nothing but a pleasant surprise. It’s a double-edged sword though. Cause of this.

  1. He takes it as a huge sign of interest and definitely plans on asking you out on a 2nd date
  2. He sees it as you passively communicating, “I don’t want him to think I’m interested so I’ll pay”.

So what you should do in this situation is offer to pay but also add. “I’d love to, I had a really good time”.

If he says, “No I’ll pay”. Let him embrace his essence of masculinity and pay. If he lets you, this is a win, win. But you sincerely offered. That’s what matters here.

6. “Seed” them throughout

What hell is that Trey!?

It sounds a little weird but essentially it’s when you start mentioning things the both of you might want to do in the future or on another date. Before you jump the gun and say, “Well goodness, Trey. I just met them”. Yes, this much is true. But you really only start seeding when you feel like the connection is great and you want to see them again.

So maybe a 1 hour to 45 minutes into the date it can come up organically like this:

Her: Yeah I think that building on 45th street is going to be a fried chicken shop or something…

You: No way!? We’ll have to try it one day.

See that’s seeding. It takes a bit of panache but if the dates going really well it won’t be hard to just casually throw that in there. You’re trying to show them that you legitimately want to see him again. Trust me, people appreciate it when you make it abundantly clear that you’d like to see them again and seeding is one of the best and easiest ways you can get there!

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Trey Hamilton

Author - The First Date Fix - Dating Coach - Content Creator -Dog Dad | follow me for some ramblings of a millennial who has dated. A LOT! TheFirstDateFix.Com