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I always made sure to ask a girl on a first date at least two days in advance. Not only did this give me enough time to make sure she wasn’t a serial killer on Google, but it also allowed me to not wash my hair for the two days prior thus giving my hair the perfect sheen. No, they never noticed, but getting my head in the game both literally and figuratively was important to make sure I was in good spirits.
It’s been documented that I would never consider any of my previous first dates as busts. For me, it was always about the mindset — having fun. The pressure often brings people down. Will you spend the rest of your life with this person? Will you tell your kids some lie about how you met rather than, “Well, we made out after eating Italian food and just kind of settled for one another”? Or will it be the last first date you ever go on?
Whatever you ask yourself ahead of the sub-$100 dinner or sub-$30 drinks you’ve committed to, those questions aren’t as important as the questions you actually ask on the date. As for me, well, I always seemed to ask the wrong ones. Favorite dog breed? Meh. Best vacation they’ve ever gone on? Who cares. Career aspirations? Okay, I didn’t ask that but I might as well have.
Instead, I should’ve asked the following.
“Do you think it’s weird that Kathleen Kelly and Joe Fox were both emotionally cheating on their significant others in You’ve Got Mail?”
If she had no idea what I was talking about, then it was a clearcut sign that I needed to “go to the restroom” and then just walk about the front door of the restaurant. Not watching You’ve Got Mail at least six times in your life is inexcusable.
But come on. It’s a little weird, right? Both have significant others yet they’re spending their nights sitting on their IBM ThinkPads flirting with one another? That’s… kind of fucked up, right? It’s a lighthearted way to get their emotional compass while also ensuring they have an appreciation for 1990s romantic comedies. Win-win.
“Did you summer anywhere as a kid?”
Proceed with caution, however, because this is a double-edged sword. If she answers in the affirmative, it means she uses “summer” as a verb rather than a noun which means you probably can’t afford her lifestyle moving forward. The good? She’s bougie. The bad? Well, you can’t afford her. The ugly? You’re definitely not splitting the tab at the end of the night.
“What’d you think of that spirited debate on Meet The Press last Sunday morning?”
And then you wait. Like, five seconds. If she begins to answer with a serious tone, then it’s clear she spends her weekends differently than I spend my weekends. If she looks at you like you looked at your elementary school teachers when they asked a question for the reading you didn’t do, then you’re in business and you just start fake laughing as if it was a joke.
Frankly, the biggest cornerstone of compatibility in my current relationship is that we’re both down to lounge on Sundays while rocking a semblance of a hangover. I can’t get up and run. I’m not trying to act like I’d rather watch Meet The Press in favor of Dumb & Dumber on Comedy Central. And the last thing I want is to get into politics while sitting down for drinks with someone I hardly know.
“Would you rather get this escargots appetizer or the calamari?”
I can deal with people who wear the same pair of pants three days in a row. I can accept that not everyone will share the same political views as me. And if I really try, I can even be down with trying to dance with someone after only having two drinks even though I have a five-drink minimum for dancing at weddings. The old college try is something that should be commended in most situations.
But if you’re a picky eater, I’m out. You don’t have to like every food out there, but you have to at least be adventurous enough to (A) try something once or (B) give me an explanation for why you’ve tried it and why you didn’t like it. I can accept at least that. But don’t take the calamari pieces with the legs — those are reserved for me. Okay, fine, you can have one of them because chivalry isn’t dead just yet.
“How hard did you Google me ahead of this?”
There are some things that you’d rather just know. Did you reverse image search me on Google or did you mail it in and just search my first name with my place of work? Did you find my Instagram profile and cycle through everyone I follow to gauge my interests, or did you just screenshot my Bumble pictures and send them to your group text? Did you find my tax information from 2011 or are you just blindly hoping that I’m not evading them? Either way, I respect it. Knowledge is power and I’d rather be informed that you know everything about me rather than drone on about my career and how I recently went on a vacation that you’ve already seen the photos from.
After all, I know you summered in Cape Cod because I saw it as your profile picture from 2008. .