In 11 years of dating in Washington, I’ve been on dozens of first dates. And I’ve made plenty of mistakes along the way. A baseball game is too much of a time commitment for an initial meeting (a rookie error I made on my first online date in 2005, back when the Nats were still playing at RFK Stadium). The hottest bar on 14th Street is too crowded — you’re likely to be mashed up against strangers, screaming over each other and having trouble flagging down a server to freshen your drink. And dinner anywhere can feel like too much, too soon when you haven’t even hugged yet.

Because online dating has lost much of its stigma in the past decade — and singles are making plans with people they know little about — first dates have gotten more casual. When you meet online, that first meetup can be more like a pre-date than an actual one; you’re assessing whether you’ve got chemistry and anything to say to each other. You might start with weeknight drinks or a weekend daytime meetup, then progress to dinner by the second or third date.

In my job as an editor and writer for Solo-ish, a Washington Post blog about unmarried life, I’m constantly talking to singles about how they meet their dates, where they like to go and what makes or breaks a budding connection.

Here are a few things I’ve learned: Starting out low-key and gradually building to more-intimate settings will help keep you from coming on too strong. Going from one place to another also allows the two of you to take turns paying the tab. By the end of a third date, you’ll probably know whether there’s potential for something deeper.

Be sure to mix up your routine. My early-date standbys used to be coffee at Tryst or drinks at Bourbon or Bar Charley. But about a year ago, I realized my favorite spots had become haunted: I’d been on so many dates there that my mind wandered from the man in front of me to other, better first dates in the same location, with someone else who was long out of the picture.

When you go somewhere so often, it’s easy to contract first-date fatigue. Suddenly you’re sleepwalking through the same date, but with a different person, and it shows. (Plus the waitstaff is probably tired of listening to your stories of that one time you did stand-up or momentarily lost the family dog.) And although first dates often involve alcohol, they certainly don’t have to. (Aren’t you tired of asking strangers to “grab a drink”?)

With that in mind, I designed these outings — Dates One through Three — with the assumption that you’re finding most of your first dates online, so you can end them easily and quickly if things aren’t going well. However, if you’ve already met in person and know there’s chemistry, jump ahead to Date Two. Whether you follow these moves or not, try somewhere new and see what that does to the energy you bring to a date.

FIRST DATE: Instead of coffee, go for gelato and a walk.

It’s a playful twist on the coffee date (which should be reserved for business, not romance). But the first time someone invited me out for gelato on a first date, I thought he was being cheap. Afterward, I realized he was being smart. If we hated each other, we could be out of there in 30 minutes and under $15.
Dolcezza and most other gelato spots offer sorbet as well, so it’s vegan-friendly, too. Start at the Dolcezza in Dupont or Georgetown, then meander through the neighborhood. From the Dupont location, on Connecticut Avenue, walk a few blocks northwest to the Spanish Steps, on 22nd Street, between Decatur Place and S Street NW. It’s quiet and shaded, there aren’t many tourists, and the nearby embassies are a conversational cue to talk about recent travel or countries on your bucket list. You can stop there, or continue through Mitchell Park and on up to Kalorama and Walter Pierce parks. If you’re starting at the Dolcezza in Georgetown, the Dumbarton Oaks Gardens are less than a mile away and offer a similar romantic, yet low-key vibe. Entry fee is $10 for adults. And remember, physical activity that gets the heart rate going can facilitate bonding. It’s hard to do that at a bar.

Dolcezza, 1704 Connecticut Ave. NW, 1560 Wisconsin Ave. NW.

Spanish Steps, 22nd Street NW between Decatur Place and S Street.

Dumbarton Oaks, 1703 32nd St. NW.

SECOND DATE: Have a drink, mixed with some friendly competition.

Like Tryst, one of my old standbys, Colony Club straddles the line between coffee shop and bar, and succeeds at both. The Park View spot starts serving beer, wine and cocktails at 5 p.m. (except on Sundays, which are dry). Grab a drink and a light snack at the bar and, once you’re ready, venture upstairs for table tennis. You can make the game a little more interesting by turning it into a challenge: Every time someone loses a point, he or she shares a fact about
themselves. For example, I learned that a recent date is one of eight kids, enjoys taking baths and, as a child, thought he would play professional basketball. Offering up random facts can be a nice change of pace from volleying questions back and forth, like on a regular first or second date. If your date is a sore loser or a total dud, you can call it a game, set, not a match and part here. Or head a few blocks west to grab a bite and another drink at the intimate, dimly lit Room 11.

Colony Club, 3118 Georgia Ave. NW.

Room 11 3234 11th St. NW.

THIRD DATE: Go ahead and make dinner reservations.

If you’re going on a third date, you’re probably pretty interested in each other. While first or second dates are often framed as the ambiguous “let’s get drinks,” which can (or can not) include food, at this point you’re going to want to make plans for a meal together. Lapis, a newish Afghan restaurant in Adams Morgan, is a great third-date spot: The dishes are creative and shareable; it can be bustling but never Le Diplomate-level crowded; and the atmosphere feels authentic without trying too hard. Which is just the mix you should be going for when getting to know someone, too. And the menu is omnivorous: There are plenty of vegetarian, vegan and gluten-free options, so meat-eaters and vegans pondering future meals together will feel full of possibility rather than stifled by limitations. After dinner, if the weather is cooperating, walk up the block to the rooftop bar at Perry’s. Nestled just far enough away from the raucous 22-year-olds on 18th Street and with a soft glow from the lights strung over the patio diners, Perry’s has a calm, grown-up feel. It’s not the hottest rooftop in town, but that’s what makes it perfect: If you think you and your date might have something lasting, what better way to show it than a nightcap at a spot that has stood the test of time?

Lapis Bistro, 1847 Columbia Rd. NW.

Perry’s, 1811 Columbia Rd. NW.

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