Dating in the District: 6 Favorite Dating Tips

Dating is mostly trial & error…and, if you’re us there are a lot of errors. Through our ups & downs we’ve had to learn some things the hard way, like a 7-hour first date doesn’t always yield great results or that accidentally drinking 3+ cocktails because you’re having so much fun might get you labeled as “extra”. As Cher Horowitz would say, Whatever. But, we’ve collected some of our favorite tips for a first date, or, at the very least less awkward.

1. 2 Hours Max: While this tip is more app specific (aka stranger dates), it can be loosely applied to all first dates. Everyone wants a good date to last forever, because, well – you’re having fun. But should it? We got this tip from one of our friends and have found it to be a great tip, if not the #1 you should follow. While these are all loose guidelines, we’ve realized that there’s nothing wrong with leaving when you’re still having fun. The same goes for finding a new job, don’t wait until you hate it or have exhausted yourself to leave. Say bye on a high note (not a low one 4 hours later).

2: Stalk: Okay, okay, you don’t have to follow this rule, but you shouldn’t feel bad if you do stalk a guy, especially if he is from an app date (psst. see our favorite dating apps for DC here). Don’t feel weird for double checking that he isn’t a total weirdo, you’re good to check out their Facebook or Twitter presence. Hot tip: make sure you’re logged out of LinkedIn before you look at his profile! One thing we will say is that not everyone has A+ social media profiles so don’t let that be the deciding factor (unless you see something unforgivable) for whether you’ll go out or not.

3. Max 2 drinks (and by 2 we mean MAX 3): As E tells me, “No Chugging.” You’d be shocked at how quickly you can down a chardonnay when you’re nervously waiting for a date. Just take a deep breath, sip a little more slowly than usual and relax. A few drinks to talk over is fine, just make sure not to go overboard you might just forget how good (or, even worse, bad) the date went.

4. Don’t lock yourself in: If are going to meet for drinks and can help it, don’t sit at a table. Unless this is a coffee shop date or some other activity date. Don’t have your first date be an activity that necessitates more than 2 hours (monuments tour, dinner, a movie, etc). You want to spend your first date getting to know someone with the flexibility of it not working out. If a date isn’t going great, you need an out – that’s why happy hours or coffee shops are our favorite first meeting places! If it’s going well, a few drinks can last as long as two hours…if it isn’t going so well, a single drink can last 45 minutes or less. Just make sure you’re in a situation where you’re not stuck.

5. Don’t be afraid to leave: This kind of ties into tip #1…but, don’t be afraid to leave. If s/he asks you if you want another drink and you don’t, say no. If s/he asks if you want to head to dinner and you don’t, say no. It can be awkward if you’re not sure if you want to stay or go but, you’ll never regret leaving as much as you’ll regret staying. Your time is precious, and if you aren’t into your date you don’t want to lead them on by dragging out the night. As long as you’re polite, don’t ever be afraid to say no. There’s nothing wrong with leaving something to the imagination and feeling like you didn’t share everything about yourself during your first chat. If it went well and you get along, you’ll meet up again, it’s that simple.

6. Bring the essentials for a touch up: Everyone loves feeling fresh pre-date so bring what you need before you go feel like the best version of yourself. No shame, everyone deserves to be confident when meeting up with a STRANGER so pack extra clothes, makeup, deodorant, or whatever else you need to be on your A game.

Although this is not an exhaustive list and I’m sure we’ll have a couple more tip lists, these are a few that always stand out for us. While they don’t need to be followed to a T, we hope you find them helpful! 💁🏼