News & Politics

Dating Diaries Roundtable

Meet our daters: Mark Drapeau | Dana Neill | Sally Colson Cline | Michael Amesquita | Kate Searby | Max Schwartz | Lucas Wall

What do you like to do on a first date? Do you prefer just drinks? Does it depend on how interested you are in the other person?

Mark Drapeau: Usually I consider drinks at a nice restaurant a good first date. There’s less pressure with the opportunity to continue things there or nearby if it’s going well, and escape if they’re not. You can also see what people choose to drink and how much, which can tell you a lot about them. I’ve never been stressed out about food and drink on a first date; personally I find activities like visiting a museum or volunteer work more exotic and harder to pull off at such an early stage.


Dana Neil: You should pick a place where it’s easy to talk. Movies or concerts aren’t good first dates. You want to see if your conversation is easy or if you struggle to keep it flowing. There’s always the tried-and-true drinks and dinner. Some people advise not to commit to a full meal just in case things don’t work out. I enjoy meeting new people and hearing about their lives, so even if it doesn’t work out I figure I’ve probably learned something new.


Lucas Wall: I like to keep a first date simple—usually drinks or coffee. I’ll sometimes do a weekend brunch or weeknight dinner if I feel optimistic. So yes, I think the plan does depend somewhat on the excitement level with that person. If I meet someone online, I’m much more likely to shoot for only drinks or coffee, whereas if I meet somebody in person and have a good first impression, it’s easier to invest in a full meal.

I always try to avoid any Friday or Saturday night first dates. This ensures there’s a time limit so if things aren’t going well, it’s easy to end the date and head home. There’s also less temptation to mess around on the first date if you avoid the prime nights. Nobody can argue with needing to get home on a weeknight to get ready for work the next morning.

Kate Searby: I like to meet for coffee or drinks on first dates. My go-to spots are Cork, a wine bar on 14th Street, Northwest, and Tryst, a cool coffee shop in DC’s Adams Morgan. Tryst provides an especially relaxed atmosphere with big, comfy couches and live music many nights of the week. It’s the perfect venue for getting to know somebody without the pressure of committing to an entire evening. If you’re enjoying yourselves, you can linger as long as you want. If not, you can comfortably part ways after a couple drinks.


Michael Amesquita: A first date equals a first impression. I’m a big believer that women want to feel like you have a plan and have given some thought to the night’s activities. I stay away from non-engaging activities like a movie or a concert for the first date. I’d definitely do a hike, baseball game, ice cream in Old Town and walking along the waterfront, or even a service project for a first date. What that first date is totally depends on what I think the person will like.


Max Schwartz: Generally I just do a happy hour, drink, or coffee date. You don’t want to commit to too much, because you don’t really know the person all that well. If it goes badly, then you’re in for a long, bad evening. Does that make me a pessimist? Generally I have no idea how into the person I am until a couple of dates anyway—so how into them I am doesn’t really factor on the first date. I guess if I felt like I really needed to impress someone, then I’d change my plans, but it isn’t like looking as though you’re trying too hard is a good thing either.