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1. Pick one thing on his profile and make fun of him for it. Did he really need to have his shirt off at that block party? Is that really his dog/baby/infinity pool or is he just using it to attract women? Making fun of someone in a light-hearted way creates instant intimacy and his response will reveal whether he can take a joke.
2. Ask him a personal question. Everyone loves talking about themselves, and trading personal stories is a great way to get things rolling (and will give you something to talk about on the first date). Just keep is light. "What's the most embarrassing thing you did in grade school?" is fun. "What's your deepest regret?" is not.
3. Type this sentence verbatim: "So, where should we get that drink?" You already know that this person finds you attractive, because they swiped right/hearted you, etc., so why even waste time on a half-hearted conversation, when the point of online dating is dating in real life, not finding a pen pal.
4. Send an invite coded in emojis: (pointing finger + martini glass + ?) Using tiny pictures instead of words somehow makes asking someone out not so intimidating. You're also displaying your prowess with an iPhone and testing his ability to translate pictures into words. Three birds. One stone.
5. Try a total non sequitur like, "Jake! Where have you been?!" I don't exactly know why, but guys really respond to this. Maybe because it acknowledges the silliness of online dating without explicitly complaining about online dating, which can come off as a bit rich since you are, you know, online dating. Maybe it's because it shows that you don't take yourself too seriously and are maybe just a little bit kooky. It's sort of like falling down as soon as you walk into a party: It's scary for a second, but breaks the ice so fast and so thoroughly that everyone can let their guard down.
6. Use a cheesy pickup line. You may have heard every line in the book, but the average male has never had someone suggest that he fell from heaven. Something that would have you eye-rolling, like, "Why is someone as hot as you looking for a date?" will probably have him messaging you back, fast.
7. Confuse the hell out of him. Open with a random emoji (nail painting is always good) and wait. If he doesn't take the bait instantly and ask what's going on, follow up with "No?" At this point, he's hooked — people cannot resist a mystery. When he responds with, "What?" tell him it was a test that he failed, but he can make up for it by buying you a drink.
8. Get a game going. Would You Rather or Fuck Marry Kill are fun ways to start a flirty conversation/suss out mutual enemies, and can almost always get a little dirty if you want them to.
9. "What's the best movie/book/meal you saw/read/ate in the past year?" A specific question about something someone will remember with fondness is a lot more interesting to answer than, "How's your week going?" Also, maybe you also loved that book/movie/food item, and now you guys have something in common and are going to be watching Foreign Thrillers with Strong Female Leads together forever!
10. Try a little role-playing. Based on a not at all peer-reviewed study, 90 percent of people using online dating apps are bored out of their minds. Spice things up by starting a role-play scenario. You're the princess, he's the prince, and you call out to him: "Oh, won't some hero come save me from this stifling castle keep!" It's a little unorthodox, but anything's better than "Sup?"