Guide to the Most Awesomely Awkward Date Ever

Dating is a delicate and sometimes uncomfortable dance. Most of us have a backlog of hot-button questions lingering in our minds when we meet someone new: How did his last relationship end? What are his feelings on marriage and monogamy [1]? Does he want children? Is he a Republican? Knowing how much to divulge and at what point requires a certain level of finesse that, quite frankly, is exhausting. Rather than sweating the etiquette, we’ve compiled a handy course-by-course guide to help you reach your highest potential of awkwardness in a dinner date and cultivate an experience that’s sure to make a lasting impression. Who knows, if he digs your blundering honesty, you may have found the one!
You Say Spring Rolls, I Say Babies
As we all know, the purpose of appetizers is to whet the appetite for the main course, and what better way to whet his appetite for what’s coming than to start off with some lighthearted breeding-related Q&A? Take the arrival of those tantalizing spring rolls as your cue to talk reproduction. Do you want a multitude of cherubs suckling at your teet? Let him know! Or are you at the other end of the spectrum and hoping to bypass the corporeal punishment that is pregnancy altogether? Do share. Nothing breaks the ice like a breezy chat about your respective biological clocks [2].
Main Course: God and Politics
Now that you’ve warmed up with some lively baby talk, as you move into the main course, it’s time to show off your worldly knowledge with a little têtê-à-têtê on current events. For the smoothest transition, lead with recent political squabbles over Planned Parenthood, abortion funding, and whether or not birth control should be free [3]. This will likely open up a robust conversation about religion and political fundamentalism, at which point you can tell him your thoughts on whether god prefers Glenn Beck, Rachel Maddow, or Jon Stewart. It also lends itself to a quick chat about sexual practices and preferences, promiscuity, exclusivity, and how many sexual partners each of you has had. Based on how all of these topics land, now you should use this time to tell him if you’re just lookin’ to utilize a little contraception tonight and get to knockin’ boots.
Dessert: How About Those Exes?
Dessert is a time to indulge and to top off the flavors of the night and each other’s wonderful personalities with something sweet. And what’s sweeter than past loves? If he’s still in the vicinity after sharing baby-infused spring rolls and a Glenn Beck–infused main course with you, venture forth with a query or two about old girlfriends. Ask him what went wrong. Tell him what went wrong with your relationships. And ask him what he’s learned. And since you’re talking exes, you may as well bring up Facebook and casual digital espionage, since it’s almost guaranteed you’re going to scour one another’s friend lists and online photos after the date to do a little background check on these ghosts from the past. If you have any anecdotes about how social media may have contributed to the ultimate destruction of previous relationships, whip them out. Who doesn’t love a completely un-neurotic stroll down memory lane?
Nightcap of Eternity
A post-dinner cocktail is the time to unwind with your date and let intimacy bloom. And if the two of you have made it this far, it’s a pretty good sign that you’ve sealed the deal—at least for tonight, which makes it the perfect time to discuss the ultimate deal-sealer: wedding vows. If you’ve had your dream wedding mapped out since you were sixteen and would like to see it happen ASAP, divulge all the sparkly details now; the same holds true if you hope to avoid the antiquated institution of marriage. When you’ve finished reciting your prewritten vows or lengthy manifesto against the institutionalization of love, ask him where he stands. Nothing prompts sweet nothings quite like a well-placed inquiry about lifetime commitment.
