I'm no expert, it's true, but dating is something I've done, and actually done well. It's different from having a boyfriend or girlfriend - it's the preamble, when you're getting to know each other and deciding if maybe, one day, y'all want to be exclusive. Confusingly, if you do eventually make it a one-on-one thing, that's also known as "dating," so for my purposes here today, that'll be known as Dating, or DATING if things get really serious.
If Generic Teen Girl Magazine approached me to write their dating advice column, where generic teen girls wrote in and basically asked me to read their crush's mind re: does he like me?, I would shrug and say yes, but only because I like generic teen girls. I always wanted to shout, "Teen letter writer! Quit being such a wet noodle and just talk to the guy! Stop writing in to magazines!" But I also understood the letter writer's dilemma: how do you conceal your vulnerable heart long enough to have a mundane getting-to-know-you conversation?
I do, however, have some dating experience. People can hit it off from the very first moment, and the first time a future couple hangs out might be a laff riot, culminating in a whisky-soaked conversation at 5 a.m. about favourite bands. On the other end of the spectrum, one party might set their hair on fire half-way through the date (ME. I have done this). In my twenties, a lot of my friends got embedded in LTRs, but I got a different education. I missed the master lessons on "how to not throttle your partner when you come home and the garbage is still a festering mess and that was the ONE THING you asked her to do this morning," but I got the community-college equivalent in "how to feign interest in someone's exquisitely boring hobbies just so you can get through the end of this glass of wine and then fake an emergency and leave."
So! Dates! Man, dates are fun. That's actually the whole point of a date: for you to go out and have some fun with a person whose genitals you might want to see later on (confidential to my mom: way, way later on. Sometime after you have your first child together). In this regard, don't shortchange yourself. For some reason, people have decided that "date" = "dinner." Dinner is boring! Take your date to the dog park and look at the puppies. (Aww.) Take your date on a brewery tour. Rent a paddleboat, browse in bookstores, get a vegan cupcake, watch a fire dancer. Fight the urge to drink loads to avoid awkwardness. Do stuff that interests you, and your potential suitors will be forced to a) bring their A-game and b) bust out the stuff that interests them on date #2. What sounds more enticing: dinner and a movie, or, "Hey, do you want to get falafel sandwiches and then go bowl a few frames? I know this bowling alley that serves crazy strong drinks." The subtext there is, "...because I am awesome."
There are some no-nos as well. I once had a date who drunkenly came home with me, made a failed pass, and then fell asleep on my couch. At some point, he sprinkled a thin layer of his belongings all over my apartment, in a crafty attempt to have a reason for another meet-up: a magazine, a book, and an expensive watch. We had an incredibly awkward second date, where he was supplicating and I was resentful, and we never saw each other again. Don't be that guy. This is also the safe-date PSA time: if you're meeting someone new, tell a friend where you're going and how to get in touch, and maybe offer a soothing check-in phone call if your friend watches a lot of sex-crime procedural shows. Most people are fine, especially if you're diligent in your douchebag filtering, but it never hurts to have a safety net.
Let's say you've introduced each other to your favourite dive bars, you've maybe had a sleepover or two, ran into some friends on the street and been totally awkward about status ("This is Eddie, my uh....This is Eddie."). Terrific. But maybe things aren't going 100% awesome, or maybe things are going better with Kyle than they are with Eddie - one of the perks of dating is that you're not exclusive until you say you are - and you need a conversation. This can be so stressful, because the are-we-aren't-we nature of going on dates. Look, you can't just drop out of someone's life, so call them up (it's fine to do it on the phone if things aren't serious/long-term) and say, "Thank you for the time we've had together lately, but I don't think we're clicking as well as we could, and I don't think we should hang out any more."
Memorize this. Tattoo it your arm, Memento-style. Let it wrap itself around your soul, if you're a hippie. My friend Suzanne recently pointed out that people will often date someone because the other person likes them, not because they like that person. Being liked is cool, and super-exciting, but if you don't dig what the other person is bringing to your table, you're not, like, contractually obligated to date them. There's no crime in realizing that you're not clicking with someone you're seeing, liking someone else better, or being bored. I have girlfriends who go back to the same guys, not because they're so in love, but because they're afraid of being alone, don't like ending it, or think the dude will change into something more desirable. Cut your losses, be the bad guy for a day or two, and move on.
One final thing: you may have to go on dozens of dates, but if you want an actual boyfriend or girlfriend, this is your tempering process, making you stronger and more knowledgeable about what you do/don't like. Pay attention! There'll be variations in age, body type, income, parent and marital status, gender, sexuality, kink, weight, height, location, and agenda. Follow your heart (barf!) and think critically about the things you want. You may discover a secret weakness for bears, or that you can't date a non-smoker, or that baristas are pretty boring when they're not feeding you coffee. Shrug. Cool. It's all part of the education.