I Went on a Date Every Day of the Week. Here’s What I Learned.

7 Dates in 7 Days? I’m older, wiser (and exhausted).

Monday was Dr. Corey from Bumble. Tuesday was Grant, a setup from a fellow comedian. Wednesday was Kevin, a super hot Tinder dude from Chicago. Thursday was Chris, another Tinder guy who worked in Marketing. Friday was writer James AND creative director Logan, a Bumble & Bumble. Saturday was Sean, a guy I met at a local bar. Sunday, I rested. JK! Sunday was a coffee date with a producer. I work for YOU!

So, in the spirit of sex, romance and everything in-between, here are seven things I’ve learned about people (especially myself) after going on seven dates in seven nights (and sometimes more). You’re welcome!

Drinking Dates Are Great (But Be Careful)

romantic dinner

According to doctors and any non-alcoholic, I drank way too much last week. Way too much. And no, it was not healthy. I’m a big fan of the happy hour date (cheap, and I love a cocktail to ease any awkwardness) but if you’re going to date a ton, stagger those date activities! I’m a gal who can definitely handle her booze, and even I was negotiating what I’ll lovingly call “Pinot Fatigue” by Thursday.

Be Aware Of Repeating Yourself (Or Forgetting What You Said)

Couple Dating

There’s so much backstory and chat built into a date- when you meet, when you text, the lead up, the conversation after- if you’re going on a bunch of dates all at once or just one every once in a while, review your text chain before you meet up to make sure you know exactly what they know about you, and what you know about them. Believe me, it can be embarrassing when you say, “So, what was it like growing up in Jersey?” When they’re from the Bay Area. Cool move, Rebecca. Cool move.

Be Thorough About Hygiene

Beautiful woman standing at the shower. is washing her hair.

I know you’d do that anyway, but when you’re meeting a bunch of new people in such little time, you’ll want to be hyper-vigilant about this. Depending on who you are, you probably wear makeup, or product, or something when you go on a date. Well, if you’re going on one date a day, you’re going to be doing a lot of prepping, making up, eyelining, cologne-ing, etc. So it’s really, really important to shower regularly and make sure you get ALL the makeup off upon the conclusion of your evening. Nobody likes to show up to a date with the person looking raggedy AF. Am I right?

The Blowout Is Your Friend

Young man paying a compliment beautiful woman

That being said, one distinct hair style for dates will cut your anxiety-laden prep time in half! I’d suggest a blowout or a flattering go-to ‘do to have in your back pocket (mine was wavy, my hair’s natural texture, with a cute, high ponytail) so it’s one element of the date you just don’t have to think about or roll the dice with. There are lots of decisions to be made on dates- place, time, how many drinks, what to wear, if you should drive…your hairstyle doesn’t have to be one of them!

Dating Is Expensive (Even With Gender Norms In Place)

Young man and woman drinking something at a cafe

I’m definitely a pay-my-way kind of gal, and while most of the men I went on dates with paid, there was definitely a financial cost to this “experiment.” Drinks, some of the time, of course. And food after you got a little too drunk (cough cough, Bumble & Bumble Friday, cough cough), and gas if you’re driving across town or worse, taking Lyft, Uber or a Taxi. There’s also data charges on calls if a date is really into texting (though admittedly that was less of a concern than my 3 am Taco Bell run). So if you’re going to date and not go full diva by demanding the other person pays or always drives your neck of the woods, prepare to take a hit to the ‘ol Wells Fargo.

The Cream Will Rise To The Top

couple picnic date

When you’re dating a bunch of people, it’s really, really easy to compare conversation, humor, behavior, attractiveness and kindness. You’ll know right away which people are worthy of a second date much better if you’re dating a LOT, and if they’re proactive enough to keep the momentum going. Keep inventory of this! Don’t second guess your gut. You have many options when you’re going on seven dates in a week or some such crazy dating binge (who would do that? An insane person!). In this case more than others, you should never feel desperate. Ever. People are everywhere and you, my friend, are a queen!

People Love Questions

Cute Couple Feeling Curious While Choosing Some Desserts

If the date is going super well or becoming a trainwreck (that was hyperbolic, I mean, if it’s REALLY going that badly, just leave!), a quick way to not feel horrifically awkward is ask questions. Turns out, people love this, it always keeps the convo going and it will take you from treading water conversationally to back into the game. It’s a no-fail way to seem desirable, social and in control. Sexy qualities, grasshopper!

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I Went on a Date Every Day of the Week. Here’s What I Learned.

About The Author
- Rebecca Leib is a comedian and writer from Milwaukee, Wisconsin whose work can be seen on on NBC, Investigation Discovery, VICE/Pulse TV, Buzzfeed, Defy, Freemantle Media and read in Reductress, LAWEEKLY, LIVESTRONG.COM, ThoughtCatalog, Art Etc., Comediva, Hello Giggles, VICE Beautiful/Decay and more. She is a freelance dating coach and love advice specialist and loves writing about dating, romance, love and relationships in the modern world.