7 Witty Ways To Snag A Second Date

Had a great first date and ready for the next one? Here are seven witty ways to snag a second date.

By Lynn Harris

he first date is only half the battle. When someone says “Sure!” to date #1 with you, he or she may not mean more than, “I should get out more — and my DVR will understand.” But saying yes to date #2? That could mean, “I should get out more — specifically, with you.”

So, how do you increase the odds of doubling your pleasure? Second dates depend on more than first impressions: they’re also about how you handle the
I should get out more — specifically, with you.
end of the first date, and the period of limbo you’re in for the next few days following it. Here are some tips from folks who have been there — and went back for more:

1. Borrow something simple
“When my date dropped me off at home, he asked to borrow a baseball cap,” says Caroline, 31. “I asked, ‘Why?’ because his hair looked fine. He said, “So you’ll see me again, if only to get your hat back.’ It was cute. And it worked.”

2. Follow up
Email the next day to say, “Thanks, I had a great time.” It’s a show of good manners and a great way to hint that you’re up for another great date soon.

3. Call it a night
Espresso, a movie, dinner, then a walk to that adorable little gelato joint? All on one date? What will you do for an encore? Sometimes, less is more, so save something for next time. Try suggesting over your espresso: “Let’s make this a really long date. How about dessert — on Thursday?”

4. Let your date pay for this one
Once your first date is covered, offer to “get the next one.” It’ll be harder for your date to turn down a free meal or outing.

5. Do what works — again
This strategy works best for casual dates with “friends” you’d like to upgrade to a more romantic status. “I made a plan to watch a Red Sox game with a woman I liked. At the end, I said I’d
I didn’t even know I wanted to kiss him...
like to see the next game with her too, and it worked,” says Duncan, 39. “Granted, a romantic strategy dependent on the Red Sox winning works only about every 90 years, so you’d do well to have a backup plan ready.” Seriously, though: People bond over exciting activities, and if you’d like your “activity partner” to bond with you, doing that same thing again helps make it your thing to do together.

6. Tell the truth — some of it, anyway
Don’t say, “My life depends on seeing you again, and if we act fast, we can get good companion fares to go home for Christmas with my folks!” Do say, “I had a great time and I’d love to see you again. Can I call you this week and we’ll set something up?”

7. Lean in for a... handshake
Shake hands and add a kiss on the cheek; you don’t want to end the date like you’re sealing a bet. But leave out the real good-night kiss, and you’ll leave your date wanting more. Samantha, 30, went out for a couple of hours — well, more than a couple — with a guy she found “great on paper” but possibly low on chemistry. His flirtatious gambit: “I’d kiss you, but it’ll be better when we’re totally comfortable with each other. You’ll have to wait.” Samantha says, “I didn’t even know I wanted to kiss him... but after he said that, I couldn’t wait for him to pounce.” And at press time, date three had gone great!

Lynn Harris ( is co-creator, with Chris Kalb (, of the award-winning website A longtime journalist, Lynn has written about dating, gender, and culture high and low for Glamour, Marie Claire, The New York Times,,, and many others. She is currently the communications strategist for Breakthrough, a transnational organization that creates pop culture to promote human rights. Submit your dating questions for Ask Lynn via
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