J, TDR Dating Challenge

TDR Dating Challenge: Don’t Get Comfortable (Day 17)

“Taking your dates to the same bar every time is like wearing sweatpants on a date” – someone who has clearly never worn sweatpants before, and the writer of today’s TDR Dating Challenge tip.

Tip #17: Find yourself bringing all of your dates to the same bar? Switch it up! Always going to the same place is like wearing sweatpants on a date.

Ummm… once again, have you worn sweats (or Lululemon In Motion leggings #obsessed) before?! That shit is WAY more comfortable than sitting across from a stranger who maybe catfished you and also maybe has no personality whatsoever for an hour making small talk! Ugh.

Ok, rant aside (I am currently wearing these sweater leggings from Express and I am angry for them because they are the MOST wonderful), let’s dive into the meat of this tip: not going to the same bar on all of your first dates.

First, I feel personally attacked. Like, have you been to Lauriol Plaza?! Have you even HAD sangrita swirl?! It is Dupont’s gift from the Gods and I will go there/make men pay for it as often as I damn please.

But also, like… I get it. If you’re going on all of your dates at the same place, a few things will happen.

  • The wait staff begin to catch onto your game (El Centro definitely did around this time last year, this is actually the secret reason I had to move), which may lead to awkward exchanges with your bartenders/waiters
  • You will begin to compare your dates to other dates you brought to the same place, allowing you to bring in additional points to fault your date that they might not necessarily deserve (ugh, he didn’t suggest we get a seat by a window so we could people watch? Jimmy just understood my interests, like, so much better!)
  • You’ll get tired! This may lead to you being more likely to cancel in favor of drinking wine on the couch. After all, a date at Rebellion is nothing new, plus you already have plans to grab a drink there with friends the next night!

So, yeah. You get the picture. I know it can be tempting to suggest places where you feel comfortable, but spread your wings, girl! My favorite strategy is to suggest the neighborhood, then let the guy decide the bar. That way I can adjust to his price point, and promptly block him from all forms of contact if he suggests Madhatter. Better to know now than on a Saturday night when you end up with a mystery hat of greenish liquor in your hands!


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