Dating can feel like a tiresome game of chess. Trust me, I know — I’ve been on more dates than I can count on my own two arms. Over the course of my experience, I’ve found that having general rules as to what behavior is appropriate at what time is fairly useful. Not only is it comforting in the early stages when I’m interested in landing another date, but it’s especially helpful later on, when I’m trying to weed out the losers from the gems.
As a favor to all the women who feel the same way, I’ve documented my learnings and metabolized them into the below set of guidelines. Give them a try next time you find yourself across the table from someone you’re genuinely into, and let me know how far they get you!
Date 1: Snack sharing
Don’t be afraid to split things like popcorn or an appetizer on the first date. It isn’t too intimate! It’s a subtle signal that you’re generous and open to connecting.
Date 2: Endearing quirks
By date number two, weird little interests like how many cats you follow on Instagram are fair game. Sharing these kinds of tidbits shows you’re willing to put yourself out there — it’s bold! Just make sure they’re not genuinely embarrassing (500+ cats) or you’ll scare your date off.
Date 3: Guilty pleasures
Guilty pleasures a la your obsession with The Real Housewives are perfect for date three. Hiding them will only do you both a disservice in the long-run. Plus, if your date shares your interests, that will be a major opportunity to connect.
Date 4: Unflattering foods
By your fourth date, you’re safe to eat spaghetti. Enjoy!
Date 5: Body bonding
On date five, ask your date to check your teeth for kale. It shows trust and that you aren’t afraid to be imperfect. Just make sure there isn’t actually food in your teeth because that’s disgusting.
Date 6: Relationship to money
After five dates, it’s okay to reveal that your relationship with money is complicated. Be sure to tiptoe around your credit card debt though; that’s best kept secret until a year or so into the relationship. Fingers crossed you get there!
Date 7: Biological honesty
Date 8: No makeup — night time
Assuming date seven’s news went over well and you guys are at the point of the occasional sleepover, experiment with washing your makeup off before bed. Just make sure the room is dimly lit, as a sort of soft-launch reveal of your non-contoured cheekbone.
Date 9: No makeup — day time
If they took your real cheek well, try showing up to your next date without any makeup whatsoever, but this time in the harsh light of day. Apologize profusely the whole time, just to be safe. If he accepts your apology, initiate the “what are we?” talk.
**If your date is willing to be seen in public with you sans BB cream, congratulations and welcome to the honeymoon phase! During dates 10-19, do your best not to engage in any new behaviors in an effort to preserve this cozy time. Who knows? The two of you might end up reflecting on it together in a few years when you’re unhappy. 🙂 Meet you at date 20.**
Date 20: Unsexy underwear
Now that you have a solid foundation, give your highest-coverage underwear a whirl and gauge his reaction.
Date 21: Skin maladies
Date 21 is a great time to get your significant other’s fingers working on your back zits. Peek at them over your shoulder during the deed, closely monitoring your S.O.’s level of enthusiasm. High = drop hints about your ring size.
Date 22: Request for help
After 21 dates, break your lease and find a new home. This may be a little inconvenient, but there’s no better way to test a loved one’s dedication than by asking for moving help. Make your 22nd date a difficult all-day affair.
Date 23: Withhold sex
See if he leaves you.
Date 24: Bathroom stuff
On date 24, sit your date down and describe the last time you had food poisoning, sparing no details. Use his response as a measure for how much he cares about you.
Date 25: Stomach-turning acts
Push things a little further for date 25 by literally vomiting in front him. Suggest that you two go for a long, winding drive or a choppy-waters boat ride. If he hold yours hair back, you really have something special on your hands.
Date 26: Leave town
I know you recently signed a lease, but date 26 is the ideal time to take a job in another town, preferably one that requires a flight to get to. See if he sticks around — no one bails on true love!
Date 27: Offensive rants
When your date visits you for your 27th, test the emotional waters by criticizing his family. If he seems offended, reevaluate everything. Does he really care about you?
Date 28: Care package
Long-distance isn’t easy, but it will put your connection to the test. Date 28 is the perfect time to send a care package containing a vial of your blood on a string. Measure his commitment based on whether it’s incorporated into his daily wardrobe.
Date 29: Your real self
Cease bathing full-stop and then hop on a plane for a visit. See if he appreciates who you really are without the toxic trappings of the beauty industrial complex.
Date 30: The truth
Text your date to look in his closet for date 30, where you’ll have left him something special during date 29. There, he’ll find the shrine you’ve created over the course of your relationship, complete with spare hairs, used tissues and skin cell samples pressed between glass. If he loves it, you’re in.
What are your dating rules?