The worst first date I went on was with a mutual friend. The stakes were high as our shared friend had insisted we had the same humor and would get along well, and because we both knew several of the same people, it had slowly turned into a highly anticipated event. But when we met, it was too awkward for both of us to show our true personalities. The worst part was that we were both heading to the same event afterwards so the date never really had a natural stopping point as we moved from one location to the other. Needless to say, we had long run out of things to say to each other when we finally parted ways. 

If you ever find yourself trapped in a date where you wish it would end sooner, hopefully you can at least get some interesting conversation out of it. And if you don’t know how to start or keep a conversation going, keep reading. 

Tell me 3 interesting things that happened to you today. 

Indeed, this is a bit crazy, especially when talking to those who are on the shyer or less talkative side, but it does help to jog people’s memories of what’s up in their lives. It also puts pressure on the other person to keep the conversation going so you can just sit back and nod along. 

I’ve been thinking about getting microbangs.

Everyone has an opinion on microbangs. This is also a good litmus test to see how comfortable someone feels lying to you. Have I considered getting microbangs? Yes. Do I think microbangs only look good on a specific type of person you only see on Pinterest? Also yes. 

here's a venn diagram of who has microbangs (in my opinion)

When was the last time you cried? 

Why waste time on small talk when we can dive right into the hard hitters? You could cry at so many things, like cutting an onion or a compilation of dogs reuniting with their owners, so this opens a lot of doors for conversation. Last time I asked this question, the response was “The girl I was talking to ended things with me and my eyes only welled up.” Whether or not your eyes “welling up” counts as crying is also an interesting conversation point. 

I love your [any current Pinterest trend], where do you get your clothes?

Whatever it is that’s currently trending, your date is guaranteed to be flattered and might even fall in love with you on the spot for noticing their unique and interesting style. Then, they might say something like “I thrifted it,” or, “It’s vintage,” even if you both know that is not true. Then, you two can begin blissfully living in a third reality where thrift stores are filled with on-trend items every season, and where overpriced vintage does not exist. 

What’s your favorite type of soup? 

This prompt is a guaranteed success; it is a catalyst for healthy and engaging non-partisan dialogue where the most radical thing you can say is that you like French onion. Perhaps you could also bring up whether or not chili should be classified as a soup, which might then remind you of my previous article that features a chili recipe.

What is your favorite modern-day Shakespeare adaptation? 

Say goodbye to pretending to know about Wong Kar-Wai or any A24 movie that came out this year. Instead, trojan horse your vast knowledge of Shakespeare into an otherwise boring conversation. Start by discussing the obvious Baz Luhrmann Romeo and Juliet adaptation with DiCaprio or the revisionist nature of West Side Story. Then, to prove how much you know about film, venture into movies like She’s The Man (Twelfth Night) or 10 Things I Hate About You (Taming of the Shrew). Maybe even mention the reimagined Romeo + Juliet currently on Broadway. Follow with: “Oh, what’s Letterboxd? I’ve never heard of it.” 

How many words in your daylist description do you actually know the meaning of? 

Spotify’s daylist, which generates a personalized playlist for you thrice a day complete with a title that is often a mishmash of random words. A sort of digitalized musical horoscope, the daylist will not hesitate to craft an entire playlist around when you listened to Twenty One Pilots once “for the mems” last night. What does it mean to have a “venting villain creepypasta saturday late night” or a “relatable microcore sunday evening?” Further, how can we reckon with the fact that we now say that things generated by AI “know us so well?” If you find that your conversation about daylists is getting juicy, try also asking them about their Spotify Wrapped, but beware: this could get real personal real quick!

Is it socially acceptable to send calendar invites for social events (and do dates count)? 

I go back and forth on this one because I do love a calendar invite and I have definitely both sent invites for and RSVPed to social events using Google calendar, but another part of me is like: what happened to playing it by ear? What happened to fun and whimsy? Why must we structure our days within the confines of the concept of time? If things are going well, send them a calendar invite to a second date. 

At this point you may be wondering, what if the person is really hot and I’m too nervous? 

How to talk to hot people 

• Exude confidence: after all, hot people are humans too. 

• Are they cool and mysterious or are they just boring? Many boring people come off as being mysterious, but once you get to know them, you may realize that they actually lack hobbies and a real personality. 

• Match the vibe. Is the person reserved and laid back or outgoing and high-energy? Without sacrificing your own personality, match the other person and remember to ask a lot of questions … people love to talk about themselves. 

• It’s a marathon, not a sprint. If it feels like they are becoming disinterested, maybe they actually aren’t the hottest person in the room. Maybe you are… 

Hopefully, these convo starters can get things going for you on your first date. If all else fails, you can always excuse yourself to the bathroom and never come back… 

- Eirian