10 Lessons I Learned After 100 First Dates

I was in a weird time in my life right after I finished college and move out to the “big” city. Being a bit too analytical, I never saw the point in dating while in college and especially not in high school, so now that I had the “grown up” job, I got into grad school, and life was pretty much figured out, it was finally time to see what this whole dating thing was about…

Not one to half-ass things, I ovaried up, jumped right in and went on multiple dates a week, here’s what I learned:

  1. “Attention World: I’m Ready For a Boyfriend!” will not yield the results immediately.
    Literally, no one cares that you’re “ready” for a boyfriend besides your mother. I love rom coms as much as the next girl (probably more) but somewhere around the dozenth guy, I realized this wasn’t going to be as easy as I thought it’d be. No matter how Type A you are, the world doesn’t fit into your carefully calculated plans.
  2. Eventually, people turn into statistics.
    I started to have ratios constantly in my head. If I plan 6 dates in a week, usually half will cancel. Of those 3, likely I’d like 2. Of those 2, if the odds are in my favor that week, 1 would also like me. If you thought about it too hard, it was kind of depressing…
  3. Time is Precious: Get offline as soon as possible.
    “What are you doing right now? I’m finally done my laundry and I’m starving. I’ve been meaning to try that new Thai place, up on Charles Street, wanna join?” Four times out of five, it worked. (There I go with ratios again).
  4. Online dating isn’t the only way to meet people.
    I spent time crafting messages, but I also talked to guys at bars, talked to guys on the bus, talked to guys at concerts, talked to guys at museums. Are you sensing a pattern? Always be closing.
  5. People that met their husbands at 19 will say annoying things to you.
    Most people have that one friend who’s basically been married since birth. I love mine but every time I had a canceled date I’d hear “Oh, I don’t know how you do it, I could never date!” as if I was so brave to be going through such a terrible struggle.
  6. Staying organized is the key to your binge dating survival.
    Mike, Josh, Travis, Mark, Shawn, Sean, Shaun… When you’re going on 3-5 dates a week, no way you’ll remember which is which. I always had my GCal up to date with the name of the dude, where we’re going and if I met them on the net, a saved his picture. Being a little creepy is better than calling him the wrong name…
  7. You have to get really good at rejection.
    It’s all fun and games (and numbers on the proverbial spreadsheet) until a guy you thought you really vibed with doesn’t return your “I had a really good time” text. If you’re in the wrong state of mind, it because a big black hole of “Oh my god, what’s wrong with me?!”
  8. You’re allowed to ask for feedback.
    Wait a few days and send a follow-up text to someone you thought you hit it off with. Once they’ve ghosted, you’ve got nothing to lose–who cares if you look a little crazy?  Miraculously, I received a response 100% of the time. I discovered a lot of dudes weren’t over their exs, that I could stand to lose a few pounds (whatever), and that some of the more free-spirited (re: starving artists) aren’t into girls in business school.
  9. Dating sucks a lot less when you go on exciting dates!
    When you’re on your 4th dinner date of the week, you’ll be desperately craving some variety in your life. Try tossing is picnics, farmer’s markets, brewery tours, and comedy shows in among the coffee dates.
  10. Don’t forget what’s most important.
    Don’t let forgettable strangers dominate your weekends. Save your most important days for people that always return your phone calls (including yourself!)


One response to “10 Lessons I Learned After 100 First Dates”

  1. Amanda Lynn Hierstetter Avatar
    Amanda Lynn Hierstetter

    Exciting dates! Although I am married, many of my friends are single and currently “dating”. Whatever that means. I think that’s the problem. Many people want a right away label, and they aren’t versed in what to do and what is proper etiquette for this. I think just have fun.

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