Modern Tips for a Mature Dater

First-date advice to help you secure a second date

The stories you tell should be fun and engaging.

Dean Mitchell/Getty Images

Alex Knott

Published March 14, 2017

Love's conquest can be broken down into five rules — at least for straight men on a first date. Whether she’s a new online match or someone you met at a neighbor’s home the other night, the following five rules should help you, the average guy, get to the second date.

It doesn’t matter if you are a seasoned pro or recently divorced and just now getting back out there — we all need work on our game.

Rule 1. Respond proportionally

If you remember nothing else, remember this: Stay within the tempo of the conversation.

Don't go on too long when she asks you a question, but also don't be too brief in your response. Too long and you are boring and self-absorbed. Too short and you are cold and about as much fun as spending the night in front of the TV with the sound turned down.

If she says a few sentences, you say a few sentences. If she tells a story, you pause and then you tell a story. You don't have to count syllables, but keeping things in proportion works wonders.

Rule 2. Don’t pay her the same tacky compliment everyone else has

Take the two most typically attractive things about her and forget them — immediately. Why?

All of her life she has heard about these probably physical attributes from other guys. You need to look past those features to get to the real her.

Rule 3. Tell her three things you really like about her

Mix it up, though. One of the three things should refer to the way she thinks. Maybe she has a great vocabulary or understanding of numbers. Or she might have a logical way of presenting information or be whip-smart or street-smart.

One quality you mention should relate to her personality. This can be anything from her taste in music or her twisted sense of humor to the way she dresses.

Everyone likes to be thought of as attractive, so there's nothing wrong with telling her in some way that she is. But don’t be crass. Maybe she looks classy or sophisticated. Maybe she has a captivating smile — or perfume.

And be sure to wait until things are winding down to tell her what you like about her. If you note her positives as they occur to you, you’ll interrupt the flow of the conversation. What’s more, mentioning them later will demonstrate how well you listen to her.

Rule 4. Come prepared with four good questions

The idea is to show her you are curious about who she is as a person, so don’t quiz her about the weather or a sports team.

One question should indicate that you did some advance research. Look at her past few Facebook posts or her Match.com profile. Then ask about things like her job. "So, have you always been into accounting, or did you have other interests growing up?"

Don't get carried away, though. It should not come across like you did hours of Google searches on her. That’s just creepy.

You’ll also want one joke question. I mean, it's not a job interview. Lighten things up. You can even have a little fun at your own expense with a question like, "So, if you were Mr. Whipple from the Charmin commercials, who would be your love interest? Rosie from the Bounty ads or Madge from the Palmolive commercials?"

Rule 5. Come prepared with five stories

You should have five good, snappy stories about yourself ready to go. If you haven’t just discovered she’s a teetotaler, maybe one of them is how single-malt scotch saved your life when you were out with your friends as Hurricane Isabel put a 70-foot tree through your house.

The tales should be fun and engaging and at least pretty close to the truth. They should not include ex-girlfriends, lewd conduct or public drunkenness. You want her to feel like she just experienced a cool four-minute movie, not a bad frat-party flashback.

Don't try to tell all five stories in one night. Remember to let her talk, too. Because above all else, it's all about rule No. 1: responding proportionally.

So these are my rules for a successful first date. They’ve generally worked well for me, with one notable exception. One time I told a woman on our first date that I’d come up with these rules but that, this time, I’d thrown them out the window — she was just too amazing. That woman is now my wife.

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