A Guide to Relentlessly Great First Dates

Whoever said “there’s nothing worse than being wrongfully imprisoned, tortured, and told the people you love have abandoned you” has clearly never been on a bad first date! But the good news is that the ol’ family recipe for great first dates starts with just one simple ingredient: a great question. Even better, the second ingredient is ALSO a great question! After that it’s watercress.

But let’s be honest! No one goes on a date hoping to have another conversation about what they do for work or how their father died (I know I don’t!!). If you ask me, it’s time to ditch the dusty get-to-know-you’s and finally get to know your date. These fun, flirty first date questions will help you break the ice and dive deep into the bone-chilling waters of love-connection!

Know any good metaphors?

There’s nothing like a good analogy. Except for a good metaphor, which is very similar. That’s why asking your date to share some metaphors right off the bat is such an awesome way to learn about the kinds of symbolic figures of speech they love most! Sometimes it helps to share some of your favorite metaphors first to get the conversation started. This is also an opportunity to be a little romantic by using a thinly veiled figure of speech from any agricultural erotica you’ve been perusing. But remember, every metaphor is a metaphor for the person speaking in metaphors. My uncle told me that.

Would you rather?

If you’re not careful, trying to learn more about a person can positively peeve them off! This fun little question gives your date a chance to share their preferences without pressuring them to communicate anything in particular, or at all.

If you could speak to animals, do you think they’d listen?

Let’s face it, people interact with animals all the time. From dogs to cats to other animals, also. It’s like we can’t get enough animals! But, no matter how many animals are out there, your date can’t talk to them. That’s why it’s such a fun conversation starter to ask, if your date could talk to animals, would they even bother paying attention? Just imagine your date talking to a squirrel and the squirrel acts like they didn’t hear even if they totally did? That would be so embarrassing!! Better to ask early on and prevent any unexpected humiliations down the line.

Which natural disaster do you relate to most?

Now that you’re a few minutes into the date don’t be afraid to open, way, way up, like a chasm. This hard-hitter gives your date a chance to express themselves, while also communicating the dread we all feel at the imminent collapse of the planetary ecosystem.

When I was 12 my Mom told me I never would have made it out of Hurricane Katrina because of asthma and lack of determination. Ever since, the devastating power of our indifferent planet has kept me up at night (but not to masterbate!!). That’s why I like to ask “what natural disaster do you relate to most” to hear about the ecological terrors that my dates see themselves in. That way I know, if they say “hurricane Ida” or “that Tsunami that decimated Sri Lanka a little while ago,” then they’re just not marriage material!

What items would you like to add to the gay agenda?

Let’s face it: you can’t avoid politics forever. If your dates go anything like mine (Gosh I hope not!), it doesn’t take too long before someone mentions the foibles of conventional arms warfare or brings up how much they’re looking forward to social security when they get older. The gay agenda can be a particularly controversial place to start, but as Leanord Niemellor, the Chaplain on Star Wars once said, “If not now, who? If not us, when?”

Read any good pamphlets lately?

I don’t care what anybody says, reading is fun! Whether it’s a short guide about coping with prostate cancer or a colorful advertisement for a Hawaiian cruise, there’s nothing that says “cozy and economical” like a crisp trifold pamphlet. Your date will love that you’re curious about the physical short-form informational content they like most. Do they read pamphlets from local doctors’ offices? Recently opened luxury apartment buildings? A rally for dentists? The Department of Defense? The pamphlets someone reads can tell you a lot about a person! Don’t miss this opportunity to connect on a deeper level, and maybe get some fun pamphlet recommendations along the way!

Which allergy is most endearing?

If you’re quick, you may be able to develop it before desert!

Where is your happy place and does it have defensible terrain?

I love hearing about those special places people hold dear. The porch where their grandma would knit and tell stories. The creek where they had their first kiss. Their family home. The local vape shop. Unfortunately, each of these locations is vulnerable to a conventional ground incursion supported by artillery fire. Their happy place will get a whooole lot sadder when the lack of mountainous terrain opens it up to strafing from a band of Grumman F-14 Tomcats, that’s for sure!! That’s why it’s fun (not to mention ADORABLE) to find out where they feel most comfortable, and then learn whether that comfort is justified within an effective defensible perimeter.

(Political) Which fictional character did you have a crush on when you were younger and where did they stand on Vietnam?

Now that the entrées are partially finished and that second glass of alcoholic seltzer is starting to set in, it’s time for things to get a little flirty. Asking about a fictional character your date had a crush on as a child (Nemo’s Dad, anyone???) is a sweet and funny way to open up the conversation! and you can preempt any awkward confrontations about American hegemony by asking for that character’s positions on Vietnam right out of the gate! It’s a win-win, and your date won’t even know it’s a competition!

What do you like to do for fun while you're awake?

There’s only so much time in the day, which is why it makes sense for people to do fun things while they’re conscious. Ask this question to learn what your date enjoys doing after they’ve woken up but before they’ve gone to bed!

Do you think bees find pollination arousing?

As the date heats up, your questions should, too ;) This zinger lets your date know that you don’t mind shifting the conversation to something a little more sultry. If you play your cards right, maybe you’ll have some “seasonal allergies” of your own!

What’s the fastest way to your heart? What about your other organs?

They say the heart is the organ of love, but if you’re looking for something long term don’t forget about the organs of renal filtration and protein synthesis. To make sure your date doesn’t turn into “the one that got away,” use this question to expedite access to their most intimate portions (kidneys, lungs, skin, etc).

What do you like to do outside of work and also outside of times that aren't work?

I don’t know about you, but I am SO tired of “so what do you do?” conversations. BORING! This question sidesteps the old cliches by asking what they do outside of work. But don’t forget, it’s SO tiring to explain to new dates what kinds of things you do outside of work! That’s why this question also sidesteps that lame convo by asking what they do outside of times that aren’t work, too! Someone get Dmitri Mendeleev, because chemistry is incoming!

Are there any sounds you’d prefer I don’t make during sex?

The date is coming to a close and it’s time to seal the deal! This question shows that you’re not only thoughtful, but subtly implies that the two of you are totally going to bone!! But who wants to bone someone who involuntarily shrieks every few minutes? Your date, maybe! So before you get a chance to ruin some intimate time with a loud, relentless growl, ask your date what kinds of sounds they’d prefer you don’t make during sex so you can avoid them.

Final tips to keep in mind

Remember, it’s not all about the answers! Some of the best conversation-starters end in a blanket of uninterrupted silence. So don’t take yawns, time checks, asking to change topic or a nearly immediate request for the check as a bad sign. They’ll come around. And if they don’t, it’s their loss* anyway!!

With these questions in your back pocket, the only problem you’re going to have on first dates is how to keep your date from proposing on the spot. Curiosity is hot, and with the right set of questions, it can be skin-meltingly scalding! But don’t take my word for it, try them yourself! I promise you won’t be particularly disappointed!

*In some cases, it’s clear you have lost as well.