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2. How do I ask someone out without coming off like a creepy stalker or like I don't care at all? How do we even toe that line?Even after we find someone we're into, asking her out is a whole other question. Do we try to play it smooth and bold, and potentially scare her off too soon? Do we avoid saying anything for three years? Do we get her number and text her a bunch until she finally asks to hang out? The options are numerous and stress-inducing.
3. Does this look like I dressed up or like my mom dressed me up? "What does this shirt say about me as a person?" we ask ourselves longingly as we stare into the mirror. We have to have a rugged but boyish charm. We need to look good without looking like we tried to look good. Ultimately, we need to wear a dress shirt and jeans.
4. Is a condom in the wallet a good idea? We don't want to look cocky or presumptuous if she happens to see a condom sticking out of our wallet, but we also don't want to be without one, just in case.
5. How drunk is just drunk enough? Should we order a few beers? Can we get so drunk that this date is no longer awkward? Will she judge us if we pass out in the bathroom for half an hour?
6. Will we be able to talk about anything beyond our favorite colors and our jobs? It's not like we need to have a passionate and undying love for the same hockey team, but if we can't both sit at our table and make fun of what the other patrons are wearing, we're going to run out of "what do you do for a living" small talk rather quickly.
7. What if the restaurant is too expensive, like five-dollar-signs-on-Yelp expensive? Yeah, we made the recommendation and intend to pick up the check, but what if the restaurant is even more than we thought? What if she picks the most expensive thing on the menu? What if our card gets declined? If we sprint out of the restaurant, will she follow? If we can psychically orchestrate a dine-and-dash on the first date, we're probably soul mates.
8. How do I establish that I'm a badass with a heart of gold? In a perfect date situation, we get the opportunity to pull off some awesome date move that makes her fall in love instantly. Maybe we'll have the opportunity to clothesline a purse-snatcher as they run by or reenact that whole "Twist and Shout" scene from Ferris Bueller's Day Off.
9. What if you talk about your ex? What if I talk about my ex? What if an ex shows up to the date?The only thing worse than having nothing to talk about is hearing about an ex she's clearly not over, or we go on and on about our exes. What was supposed to be a date turns into a therapy session.
10. What if I spend the night alone at the restaurant petrified of making eye contact with anyone else because I get stood up? "Oh, me? No, I'm not waiting for anyone! I just got all dressed up and came to this place to play Flappy Bird on my phone while I sit at a table by myself."
11. Is there such a thing as too many bathroom breaks? What if we have to pee in the middle of dinner and leave you alone? What if we have to do that more than once? What's worse: leaving the table multiple times or peeing our pants?
12. What if my favorite joke doesn't get any laughs?There are few things as quiet as the silence that falls over two people after one of them tells a joke the other person doesn't find funny. It's the sound of a kitten gently walking on freshly fallen snow, crying silent tears.
13. Is she different than my first impression? What if that great first impression was a complete fluke? Maybe we were both really drunk, and bonding over the game of Survivor Flip Cup we won together isn't a solid foundation for a relationship.
14. What if she's not impressed with us? What have I even accomplished? Should I bring my old soccer trophies to show off casually? We don't want to disappoint. What is it you even like about us, and how do we play that up as much as possible and downplay literally everything else?
15. What if I completely forget how to kiss? I'm pretty sure most people just black out when going in for a kiss and go straight from leaning in to kissing because the whole idea of a first kiss is so awkward your brain shuts down as a defense mechanism.
16. What if there's a second date? There's a sense of relief when we have that moment where we get to leave an awkward date and walk out into the night. We know we'll never see each other again, and it feels kind of like getting off a roller coaster: It might have been touch and go there for a while, but we survived. Way scarier is the prospect that the date went well, which means a second date, which means we have to start this process all over again…
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