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Wellness > Sex + Relationships

Jess and Katie Take You on the Best Date Ever: The Timeline Of A Date

We love dates. We like that stupid yawn-stretch-arm-around-her move boys pull at the movies, and the “So-how-do-I-do-this-again?” trick girls do at bowling alleys. Dating is as all-American as watching baseball or stealing land from indigenous people. But in this age of rampant random hookups, we fear the date is fading away. So, as Justin did with sexy, we are bringing dating back. And not just any date. The Best Date Ever ©. Pop some breath mints and get your game face on, because we’re going to take you out.

STEP ONE: INITIATION Making the first move is easy and also easy to screw up. Let us guide you.


  • A little recon (through Facebook and friends, not background checks) and get to know his interests. If he loves, um, penguins, then casually ask if he’d want to go to the aquarium’s Antarctica exhibit. He’ll be like, “Oh my God. You like penguins too!!?,” and you can share in his dorky curiosity. If all goes accordingly, your night will probably end like this.
  • Tell him there’s a new restaurant that you’ve been wanting to try and that you should go this weekend. Men like food.
  • Keep it cool, confident and casual, and always smile, particularly if you’ve blown thousands of dollars and several years of your awkward stage picking popcorn from your braces and have gorgeous teeth to show for it.


  • Ask him out via a friend of his or yours, Facebook message or text (see: First-Time-in-a-Text-er)
  • Reveal that you did your research and memorized his Facebook interests, musical preferences, etc.

MYTH: The guy always has to do the asking
This isn’t your prom. Have some metaphorical balls and ask for what you want. [pagebreak]

We’re English majors, but we acknowledge this step may require some math.

Solving Your Sartorial Conundrum:

  • Factor in the nature of your outing, and outfit accordingly. No extra credit awarded for showing up to a baseball game in heels or a ski trip in a bikini
  • If your entire outfit costs more than six times the cost of the date, you’re probably overdressed (exception: if your date somehow involves no spending, don’t go naked).

The Location Equation: Don’t change his plans, but if you’re the decider, keep this in mind.

  • Bad ideas: Restaurants at which you can’t pronounce the food, your parents’ houses, overly romantic settings (too soon), the dining hall (it’s cute if he offers to swipe you in, but … oh wait … it isn’t.)
  • Good ideas: mostly everywhere else on the planet
  • Best idea: Baskin Robbins, the location of Barack and Michelle Obama’s first date. And as Mr. Prez recalls, “I kissed her, and it tasted like chocolate.” Moral of the story? Take your guy out for a mint chip sundae because then he will probably be president one day.

First date, clean slate. Talking seems simple (… you do it every day), but there are a few topics you just shouldn’t touch.

Major Mistakes:

  • Talking about GPAs, salaries, weather, the stock market or anything that involves excessive digits; discussing past relationships (If Joseph Gordon-Levitt can’t pull it off in 500 Days of Summer, you definitely can’t), drinking to the point of bad drunkenness, talking shit about people.

MYTH: The guy always pays
It’s the 21st century and we’re in a recession. If you asked him out, you should at least offer to go halfsies. When he more than likely grabs the bill and says he has it covered, you can give a fake “Are you sure?” (… of course he’s sure). It’s the polite thing to do, and let’s be real: it will rarely result in you opening your wallet. [pagebreak]

It ain’t over till it’s over. So, um, when exactly is it over?

The Doorstep Moment

  • If thinking about kissing him makes you throw up in your mouth a little: Don’t. Just don’t. That is, if you hated him. If you lacked chemistry but he was a nice guy who revealed no common cold or mono-like symptoms, just be nice and kiss him. It’s ten seconds of your life but is probably the highlight of his week. Or year.
  • If you want to make out but think your underwear looks better on you than the floor: We find the how-far-will-you-go tango with boys to be kind of hilarious and wonderful, because it reminds us that even in this cynical age, hope still exists. Oh, boys who think all they have to do to get lucky is hold our attention for more than 20 minutes! Anyway, do what you want; if he thinks you’re a tease, it’s his problem. Boys who judge girls end up sleeping alone (that, by the way, is also his problem).

MYTH: If you have sex on a first date, you won’t get a second date
Jury is still out on whether this is wise advice from savvy daters who’ve been there or a lie spread by bitter girls who never get laid. You should not, however, justify first-date sex by saying to yourself, “It worked for Carrie and Big!” Because guess what? Carrie Bradshaw is NOT A REAL PERSON. That being said, we know a girl who knows a girl who ended up marrying the guy she screwed on a first date. So it could happen to you too. Oh, we should probably tell you to be safe. Don’t turn a positive night into a positive … you get the idea. Basically, don’t do this:


Because we’re assuming you’d like to see him again.

The Morning After

  • If you ended the night on your doorstep: next-day texting is better than waiting three days to call. We’re the 24-hour news cycle generation. Just don’t ruin a great date with shitty texting.
  • If you wake up in the same bed: letting him use your shower is optional — think of your roommates — but letting him eat some of your cereal is a mandatory gesture.

FUN FACT: 95 percent of girls who followed our advice got second dates … And the other 5 percent weren’t looking for serious relationships anyway.

Katie most enjoys friends, non-fiction, and dessert. She graduated from University of Pennsylvania and is a contributing editor at Glamour magazine.
Jess (Penn ’11) left her Pleasantville-esque hometown of Berkeley Heights, New Jersey to study English and creative writing. At Penn, she has been an editor of 34th Street magazine and its blog, underthebutton.com. Jess is also the Adventure Editor of The Lost Girls travel website. If you find a way to score her Bruce Springsteen tickets, she’ll probably marry you or at least make out with you. She had a pretty deprived childhood (no TV allowed on school nights) and is compensating for lost time by consuming pop culture like Don Draper downs martinis. This summer she worked as the entertainment intern at Seventeen magazine, where she hugged Kellan Lutz. Unrelated fun fact: Jess is a book nerd who will read just about anything that is not a Twilight book. Sorry, Kellan.