How to Score More First Dates


You might think that planning a first date is a pretty routine affair these days. That’s because if you’re doing online dating, you’re going to go on a lot of them. Here’s how it should go down: Guy chats with girl. He suggests meeting. They settle on a place and time. They go on the date and are so enthralled with each other that they text each other smiley face emoticons as soon as they get home.

The point of the first date is to get you a second date and start the process of building a relationship. However, it’s shocking how many things can go wrong from the time you write “It would be fun to get together” to the moment you are sitting across from one another swirling your Syrah.

Yet possessing stellar first-date skills is especially important this time of year during online dating’s high season. That’s when the largest number of people subscribe to dating sites. That means there’s more competition than any other time of year, and a guy with date-planning game is going to beat out one who lamely writes, “Let me know if you ever have some free time in the near future to grab a quick coffee or something, if you feel like it.”

Note: I’m assuming traditional gender roles here. Even if you don’t embrace them, the reality is that the many daters are, and a lady is likely waiting for the man to take the lead. Read (“First Dates: Who Should Pay … and Why”)

Here’s a list of common problems and ways to fix them:

1) They wait too long to ask for the date.

There’s a sweet spot during communication when it’s wise to ask for the first meeting. You don’t want to write “I loved what you wrote in your profile. Can I take you to dinner?” At the same time, few people have the time or patience for weeks-long correspondence before someone suggests actually going on a date. Exchange a couple emails to establish some rapport (“I saw you’re a cyclist in your photo. Can you recommend some good trails around here?”) Maybe chat on the phone once. Then close the deal by asking “Would you like to meet up?”

2) They don’t make specific plans.

Asking a woman directly if she wants to go on a date is very different from vaguely stating “Give me a shout if you want to hang out sometime.” Even if your match really wants to meet you, she might feel too forward to forward you her Google calendar.

After asking if she wants to meet, then present a detailed plan, such as “Would you like to meet for a glass of wine next Tuesday or Wednesday?” Bonus points if you suggest a place. Although there seems to be a lot of pressure these days to plan a super creative first date (Stand-Up Paddle boarding Groupons! Truffle-making lessons! Karaoke!), the best dates are simple meet-ups that should last no more than a couple hours. You just want to chat and see if there’s an attraction.

3) They don’t confirm the date.

We all have busy lives and packed schedules, so it’s not uncommon to plan a date at least week away. It’s good manners to confirm at least a day or two before that it’s still on your calendars. It’s hard for a woman to get excited about a date when she receives a text at 3 p.m. reading “Still up for meeting tonight?” On that note, don’t ask if someone “still” wants to get together. Show off your confidence by writing, “Just checking in … Looking forward to meeting at Vino Vino tomorrow night.”

4) They suggest meeting halfway.

If you live more than 10 minutes away, asking someone to meet you in the middle is certainly “fair.” But it’s not romantic and comes from a place of caution. A woman might agree to make the drive, but she’s going to notice that her Thursday night date came all the way to her neighborhood for their first date. So make the trip. You can suggest meeting closer to her workplace, if that’s more convenient.

5) They don’t mention a second date.

It’s not fair to mention going on another date if you’re not feeling it. But if you are, a woman always appreciates hearing “I had a great time. I’d love to see you again.” Then get to work planning a fun second date idea.

About the Author:

Sarah Elizabeth Richards is a journalist and the author of Motherhood, Rescheduled: The New Frontier of Egg Freezing and the Women Who Tried It. Her writing has appeared in The New York Times, The Wall Street Journal, Marie Claire, Elle, Cosmopolitan, Slate and Salon.

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