50 Non-Pandemic-Related Questions to Ask People on Dating Apps

My #1 online-dating pet peeve is bad conversational skills. It doesn’t exactly bode well to begin an exchange with someone you presumably hope to impress by merely saying “Hi.” Sure, maybe that works in a bar setting, where a person can get an immediate, at-a-glance sense of your vibe/style, but a Tinder inbox requires more from you than that. To be interesting, you have to be interested.

That said, we’re at a strange moment in history (to say the least) where “What’s up?” or “How’s it going?” can come across as oblivious or even insensitive. (How the fuck do you think I’m doing, Chad??) But you also don’t want to veer too far into commiseration land, because the trials and tribulations of quarantining are not exactly fun, fresh, flirty conversation fodder. So what’s a modern dater to do?

I’ve come up with 50 questions you can ask someone on your dating site/app of choice that have nothing to do with the pandemic situation. Sure, it might come up in some people’s answers, but only if they want to go there. Asking fun questions in your opening message is always a good idea, but particularly so at a time like this when everyone wants a dose of escapism and connection – that’s probably why they’re looking at their dating-app inbox in the first place. Try some of these and let me know how it goes!

  1. What’s the best piece of advice anyone ever gave you about [romance/business/creativity]?
  2. What song or album are you obsessing over right now?
  3. What’s your favorite memory from childhood?
  4. What’s your go-to comfort food?
  5. When you were a kid, what did you want to be when you grew up, and how does that relate to what you do now?
  6. Who is the most famous person you have met?
  7. What’s an outfit you feel amazing in and why?
  8. What’s the best thing you know how to cook or bake, and how did you learn to make it?
  9. What’s a movie you wouldn’t necessarily say is your all-time favorite, but that you love nonetheless?
  10. What’s a weird inside joke you have with a friend and how did it start?
  11. What’s a common misconception about your job?
  12. What was the last book you read, and did you enjoy it?
  13. Do you feel like you’ve found your “life purpose” yet?
  14. What country would you like to move to if you had the chance?
  15. When was the last time you did something that made you nervous?
  16. Did you have any weird hobbies when you were a kid?
  17. What’s your morning routine?
  18. What’s your favorite holiday?
  19. What is the wildest lie you’ve ever told?
  20. What’s your favorite scent?
  21. Who would you consider a hero of yours and why?
  22. What do you keep on your nightstand?
  23. Are you an introvert or an extrovert?
  24. What part of your body do you like the most?
  25. Who was your favorite teacher in school and why?
  26. What would you do with your time if capitalism was abolished?
  27. What’s your favorite word?
  28. What role does social media play in your life, and how do you feel about that?
  29. What’s your favorite thing about your home?
  30. What celebrity do you think would make a really great roommate?
  31. Which fictional character do you most identify with and why?
  32. What’s a piece of media that can reliably make you cry?
  33. What’s a task most people don’t like doing that you actually enjoy?
  34. What do you think will be the biggest technological innovation in our lifetimes?
  35. If you were famous, what would you want to be famous for?
  36. What’s an item of clothing you wish you owned?
  37. What makes your best friend so terrific?
  38. What’s the last problem you solved?
  39. What’s one of your hidden talents?
  40. What’s the most athletic thing you’ve ever done?
  41. What’s a social rule or expectation you totally ignore?
  42. What’s the most common compliment you receive?
  43. What’s the best kiss you’ve ever had?
  44. If you were going to start a podcast, what would it be about?
  45. What’s an out-of-character decision you’ve made recently?
  46. What’s the best Halloween costume you’ve ever worn?
  47. What’s something you love, without really knowing why you love it so much?
  48. What’s a bad habit you’re trying to break?
  49. What’s the fanciest event you’ve ever been to, and what did you wear?
  50. What question do you wish more people would ask you?

12 Days of Girly Juice 2019: 4 Fun Events

I got to attend many fun and eye-opening events this year, in Toronto, New York, Portland, and Montreal. It was hard to pick just 4 to highlight here, but these were really the standouts…

Tinder Live

Comedian and author Lane Moore tours the continent with this fabulous show, in which she sets up the screen of her iPhone to project onto a wall so the audience can see it, and then literally just… Tinders. Live. There are a few rules – she only makes fun of men, for example, since women and non-binary people get their fair share of harassment already – but mostly you just get to watch a hilarious person have silly Tinder conversations with random strangers. Attending this event was such a light-hearted balm for my Tinder-weary heart (why is everyone on that app a terrible conversationalist?!) and helped me once again see dating as less soul-sucking and more playful, joyful, serendipitous. Thanks, Lane!

Suicide Intervention for Weirdos, Freaks, & Queers

(Content note for this one: suicide, suicidal ideation.)

Carly Boyce – who my longtime readers might remember as a tarot reader who’s given me some much-needed illumination and encouragement in the past – teaches a truly incredible workshop on suicide intervention that I was lucky enough to get to attend this year. Carly led a discussion on suicide-related myths and fears, and then offered some concrete strategies for keeping your loved ones and yourself safe when suicidal feelings come up. I took many, many notes during this session that I’ve subsequently frequently referred to, when I or someone in my life was feeling unsure about staying alive – unfortunately a not-uncommon thing – and each time, I was so glad to have these tools under my belt. Thank you, Carly, for the knowledge and light you put into the world.

XOXO

I was lucky enough this year to get to attend XOXO, “an experimental festival for independent artists who live and work online” (that’s me!). I was nervous, because it’s a big conference full of big personalities and I am a smol shy weirdo, but it ended up being an incredibly welcoming and safe-feeling space for me. Some of my favorite talks included Lindsay Ellis‘s reflections on being hounded by trolls, Emma Kinema‘s inspiring words on the importance of unions, and Hbomberguy‘s heart-warming tale of a wacky fundraising drive. The nightlife at XOXO was my fave, though – I still think fondly about the night I spent watching Pump Up the Jam and the Allusionist do live podcasts and laughing so hard I couldn’t breathe. I hope to be able to attend XO again next year!

Blunderland

I was introduced to the House of Yes and their frequently sold-out variety show Blunderland by my clever friend Bex, and I’m so glad. It’s a raunchy night of over-the-top amazingness: burlesque, slapstick, storytelling, music, aerial silks, and more. An honorable mention goes to the House of Yes’s production of A Midsummer Night’s Dream, which I also got to see this year; I’ve never seen a queerer, kinkier, poly-er adaptation of that play!

What were your favorite events you attended in 2019?

5 Rules For Better Online-Dating Interactions

Online dating is a beast. If you’re not careful, it can consume your life, with its alluring promises and gameified interface. This is especially true if, like many of us, you’re just not finding it that useful for its purported purpose: connecting you with people you’ll get along with. Sometimes Tinder, Bumble, and OkCupid can feel like a pit of quicksand that sucks up all your time – and crushes your soul in the process. I often compare it to trying to find a diamond in a garbage heap.

In recent years, I’ve tried to streamline my online-dating habits by imposing a few rules on myself. These make my time on these sites and apps more efficient, by narrowing down my dating pool to only people I might actually enjoy talking to. Here are those rules, incase you want to try some for yourself…

Delete any message which does not specifically reference you/your profile.

I decided to implement this rule upon my most recent OkCupid rejoin, and as much as it is frustrating sometimes (SO MANY people just write “hi” or “hey,” or have clearly copy-and-pasted their message to multiple recipients!), it also simplifies things considerably. I no longer have to pick through every message-sender’s profile trying to decide if they merit a reply; the vast majority of contenders are taken out of the running immediately because they’ve failed to do the absolute bare minimum to even qualify for consideration.

This might seem like a harsh rule, but the more I think about it, the more sense it makes. Whether you’re looking for a one-night stand, a long-term relationship, or anything in between, you want to connect with people who will put effort in. Good sex requires effort; good dates require effort; sustaining any kind of relationship requires effort. If someone puts in almost zero effort from their very first message – when they should theoretically be trying the hardest to impress you – then that attitude will probably extend to other aspects of any potential relationship as well. Hit “delete” and make room for people who are actually trying!

If someone doesn’t ask you any questions or give you anything to ask them about, stop talking to them.

Some people are bad conversationalists. While it’s nice to pick up the slack for them and try to make a convo work in spite of their shortcomings, it’s not necessary. Yet again, this comes down to effort. If they answer your every question like you’re doing an informational interview, and never ask you anything, frankly they don’t deserve the pleasure of talking to you.

There are exceptions, of course. Some people are neurodivergent in ways that affect their conversation style, and some people are just better in person or on the phone than they are via text. If you get the sense from someone’s profile that they might be more interesting than their shitty messages have led you to believe, feel free to give them another chance in a different setting (like a phone call, or an actual date). But you are not at all obligated to. You are an interesting, fun person and there will be other people who are more than happy to have fabulous, engaging conversations with you.

Don’t look at someone’s profile for very long before messaging them.

I would say that on a platform with short profiles, like Tinder, you shouldn’t spend more than a minute looking at anyone’s bio – and on sites where profiles provide more information, like OkCupid, you should give yourself 3-5 minutes, tops. Online dating can be staggeringly time-consuming, especially if you fall into the trap of thinking you have to know you’re into someone before messaging them. Your gut feeling about a person is probably accurate, whether you find them intriguing or boring.

Some people online-date like they’re picky eaters wandering through a grocery store, examining each vegetable for discolorations, carefully reading every ingredient on the back of every cereal box. Others online-date like they’re grocery-shopping while hungry for a particular meal: they speed-walk through the store, mercenarily grabbing each item they need and shoving it immediately into their basket. Research about the paradox of choice shows us that people who spend a long time weighing the pros and cons of each option actually tend to be less happy with their eventual decision. So don’t waste time poring over profiles in an effort to understand the minds of strangers you might not even ever have a conversation with, let alone a relationship. Get in, get out, and then get back to your life.

If someone’s profile makes you laugh or smile, message them to tell them why. (Unless it’s mean.)

Try not to overthink this too much; make like Nike and just do it. Sparks of recognition or excitement while reading someone’s profile are depressingly rare – “Hey, I get that joke!” “I watch that TV show too!” “This picture is so goofy and cute!” – so you might as well chase them when they crop up. These are the types of shallow cues that can lead to a deep connection if pursued, so keep an eye out for anything in a profile that authentically delights you.

Of course, you can just send a quick note saying [x thing] cracked you up or piqued your interest, but you’re likelier to get a good response (or a response, period) if you add at least one question. If they referenced your favorite show, ask them which episode they love the most and why, or which character they most relate to. If they’re posing with a parrot in a funny pic on their profile, ask them about the circumstances that led to them meeting a parrot. You get the idea.

Suggest going on a date as soon as you’re comfortable doing so.

When I first started online-dating, I only wanted to physically meet up with someone after we’d chatted via text for at least a few weeks. I wanted to feel fairly certain that this new crush wasn’t a serial killer (or an awful conversationalist) before agreeing to hang out with them. I also wanted to learn enough about them to determine whether I was attracted to them. But I realized pretty fast that you can actually gauge all of these things better in person than you can via text. Even the most suave texter can be horrible in person, or at least just not what you were expecting. Better to find that out sooner than later, I say!

The easiest transition into a date-ask is to bring up an activity or event that the two of you might be interested in checking out together. If they mention they’re into improv, tell them about a specific show that’s coming up and ask if they’d like to go with you. If they say they like cocktails, ask if they’d like a date to that cool new cocktail bar that just opened in your city. Whatever it is, make sure it’s specific and soon, ideally within the next week – any longer and you could lose interest, or they could, or both. If and when the date actually happens, you’ll be able to learn quickly whether this potential relationship is destined to soar or to fall flat.

 

Do you have any rules for yourself when you look for dates/hookups online? What are they?

5 Features I Wish All Dating Apps Had

Dating apps are exhausting. As App Store searches and online reviews here will attest, there are soooo many of them – a surprising amount of which are more gimmicky than functional.

I’m dating an app developer, so I could just complain to him about all this. But I’m a blogger, so you get to hear about it too. (You’re welcome…?!) Here are 5 features most dating apps don’t have, which all of them should…

Actually useful filters. There was a time in OkCupid’s history when you could set certain answers to certain compatibility questions as “mandatory” for your potential matches, and the site would hide people from you who didn’t answer the way you wanted them to.

This feature could be used to swiftly expunge from your dating queue anyone who – for example – held racist/sexist/homophobic beliefs, felt differently from you about eventual marriage or procreation, or even just… didn’t like giving oral sex. (Hey, we all get to decide what’s important to us in a potential partner!)

Many of the site’s filtering features are now reserved for paid users, and it’s a real shame. I don’t want it to even be possible for me to accidentally strike up a conversation on OkCupid with a Trump supporter, a selfish lover, or someone who thinks women are morally obligated to shave their legs. I should be able to erase them all from my world in one fell swoop.

Comprehensive blocking. Internet safety has become a bigger and bigger issue as the online world has interlaced with the “real world” more and more – and yet many social networks and apps still don’t take it seriously enough.

Tinder, for example, lets you block someone you’ve already matched with, but doesn’t let you block people who just come up in your swipe queue – which is a problem if, for example, you spot your abusive ex on the app, or someone makes multiple creepy accounts in an attempt to contact you, or you just keep running into the same douchebag over and over.

If a dating app values safety – especially the safety of its most vulnerable and marginalized users – it should provide a blocking feature which works, completely and immediately, no questions asked, and which can be used on anyone you encounter in the app, not just people you’ve matched or messaged with.

First-message length minimums. One-word messages are an epidemic on dating apps. “Hi.” “Hey.” “Sup.” Frankly, I think that if you only want to put that much effort into dating, you’d be better off posting on Facebook to solicit dates with former high-school classmates, or trotting down to the local bar and shouting “Anyone interested?!”

OkTrends, OkCupid’s now-defunct blog of dating-based statistical analysis, found that the ideal first message length is 200 characters – so, about the length of a tweet, but like, a substantial, thought-out tweet that you didn’t dash off in five seconds.

Granted, not everyone’s attractions work how mine do, but if it were up to me, I would instate an 100-character minimum on first messages in every dating app. Read your potential match’s profile and find something to comment on or inquire about; if you can’t do that, then why are you even interested?

Organization tools. Okay, not to sound like a total slut or a total nerd (I’d rather be equal parts of both), but sometimes I wish my Tinder inbox had folders.

Kind of like how I have one Airbnb wishlist for far-away destinations and one for weekend getaway spots, I need a Tinder folder for “potential relationship material,” one for “could be a fun hookup,” and one for “you already went out with this person and it didn’t go well – beware.” And that’s just for starters.

If it sounds like I’m reducing people to their objectlike utility, well, I probably am – there’s a reason the phrase “meat market” persists, despite our better intentions – but I also think the ability to sort matches would help cultivate more actual, IRL connections. Part of the reason I so often forget to message people is that by the time I’m in the mood to reach out to someone, the cuties I was most excited about have often been pushed down in the queue by more incoming matches. If I could find the most promising among them, quickly, whenever the mood struck, I’d be likelier to actually make contact.

Activity-based statuses. Tinder had the right idea with their “Matches Up For…” feature, which allowed users to mark themselves as “up for” drinks, coffee, and a few other boilerplate date activities. But what dating apps really need is a blank field where you can type whatever you’re up for.

True, this feature would be abused immediately, by people who don’t understand that nonconsensually showering strangers in dicks is a dick move, even in text form. But just imagine how good it would be if it worked. “Up for… seeing the Harry Potter improv show at Comedy Bar tonight.” “Up for… a marathon viewing of The L Word over Chinese delivery.” “Up for… co-working at a coffee shop, with intermittent flirty eye contact.” Being able to articulate whatever weird datelike activity you’re craving, and maybe actually find someone who wants to do the same thing, would be blissful.

This feature would, of course, be useful for sexxxy purposes too. While there are lots of times I’ve just craved sex, it’s far more common that I crave a specific sexual act. “Up for… a thorough paddling from an experienced, sadistic dom.” “Up for… no-reciprocation-expected cunnilingus.” “Up for… a handjob while listening to Vivaldi.” Some apps go to great lengths to determine your sexual compatibility with potential matches, but I think knowing what someone wants to do in bed right now might give you an even better window into their sexuality than their answers to prefabricated questions, which they may have answered months or years ago anyway!

What features do you wish all dating apps had?

 

This post was sponsored. As always, all writing and opinions are my own.

Love Addiction, “The Pisces,” and Me

I’ve never been addicted to a substance. I’ve never been over-reliant on booze or weed or pills. But I have been addicted to romantic fantasies, and let me tell you, the compulsions and withdrawal can feel surprisingly tangible – like something vital is missing from your blood, your bones, and you’d do anything to get it back.

In the last few dying weeks of 2016, I went on a Tinder date which was completely unremarkable, except for what I learned from it. My pre-date banter with this boy was fast and easy, creating the sense of chemistry where perhaps there was just empty charm. The date itself was boring, one of those classic Tinderludes where you work painfully hard to pull dry conversation out of a monosyllabic, nervous stranger. The sex that followed was boring, too: our bodies didn’t fit together right, we didn’t take each other’s hints or make each other giggle, we just loped through the encounter as if on hookup-culture autopilot. The boy left around 2AM and I snuggled up in my bed, alone.

It took me until the next day to realize something was wrong. I felt a profound heaviness in my body, like when I’m hit by depression, yet even more acutely needling. It felt like something I loved had been abruptly taken away from me, even though – much to the contrary – someone I didn’t love had left me alone.

Dissecting these feelings in my journal, I saw that I’d put a lot of stock into this boy in the few days we’d known each other. I’d extrapolated wild compatibility from his brief texts and bland emojis. I’d spun our present into a plausible future. I’d imagined he wanted more from me than just sex, and I’d imagined wanting anything from him. So when the date itself was a disappointment and the boy left, I was shaken – not by the loss of the boy, but by the loss of the fantasy.

This had become, I realized, a pattern in my life. Compulsive swiping was how I dealt with any uncomfortable emotion, from boredom to sadness to fear. No matter what, it felt safe and sparkly to return to a reliable old fantasy: that this next swipe, this next match, this next message would lead me inevitably closer to the love of my life. That I was moments from a meet-cute that would cure my every sore spot. That someone perfect would come along and relieve me from the mundane inadequacy of myself.

The trouble is, when romantic fantasy gets you high, you crash spectacularly hard whenever your romantic hopes are dashed. I saw this in the months to come: a sexting pal told me he was unavailable for a more romantic situation, and I cried; a Tinder match told me he wasn’t actually interested in me because our views on polyamory differed, and I cried; a new FWB stated clearly that he didn’t want me in a romantic way, and I cried. A promising OkCupid boy ghosted me after less than a day of scintillating texts, and I had a total meltdown: nausea, panic, weeping, unsalvageable despair. When the pain of that rejection became unbearable, what did I do? I hopped on Tinder to find someone else to fantasize about. (That next distraction eventually ghosted me too.)

I was in therapy all the while, and probably not being altogether honest about the extent of my addiction. But my therapist, ever-perceptive, asked me once, “How much time would you guess you spend on online dating every week?” and I couldn’t quantify it. There were the hours I spent swiping, and the hours I spent moonily fantasizing, and the hours I spent going on dates, and the hours I spent crying and journaling when the dates didn’t go perfectly. The total seemed incalculable – partly due to the shame of that calculation.

Somewhere around this time, a friend of mine started going to weekly meetings for sex and love addicts. I was surprised to hear this; she had always seemed so level-headed. But looking back, I saw places where maybe our kinship and connection had been based on a shared addiction: we loved debriefing about boys and dates and minute flirtations, and we encouraged each other in these fancies. Where was the line between healthy fun and self-destruction?

Though I wasn’t sure whether my friend’s condition was anything like mine, the phrase kept returning to the forefront of my mind: love addiction. It seemed to fit. The highs of my fantasies were euphoric, like that first sweet hit of a new drug – and the subsequent devastations felt all-consuming, closer to rock bottom every time. In those depressed states, I’d hunt for something, anything, to relieve my sense of loneliness and failure. Alcohol, drugs, shopping, self-harm, exercise, bad TV, more Tinder time – nothing could fill the void. It felt like I needed love, but really what I needed was a healthier relationship to love.

I went to see another friend of mine who had struggled with multiple addictions in the past, and had been through a couple of twelve-step programs. As we sipped milkshakes in my pal’s apartment, they told me, “When I find myself wanting to do something rash, I always just tell myself, ‘If I still want to do it in 15 minutes, I can.’ And I almost never do.” I took their advice to heart: distraction, I knew, was not a long-term strategy, but maybe it could help shake me out of my addiction just enough that I could start recovering.

And recover, I did – slowly, non-linearly, with the help of a therapist and my friends and intermittent partners and lots and lots of writing. Nowadays I can browse Tinder occasionally without hanging my entire livelihood on each swipe, and while I haven’t been on a first date in months, I gather the day after a date would no longer make me feel like death. I’m still careful and self-critical about these behaviors, but I seem to be doing okay.

I hadn’t thought about this stuff in a long time, but then I picked up Melissa Broder’s new novel The Pisces and felt like I was peering through a looking-glass at my early-2017 self. So it seemed like a good time to examine my history with love addiction and write about it here.

Broder is the biting writer behind the viral @SoSadToday account on Twitter, the subsequent depression-soaked essay collection So Sad Today, and a book of poetry called Last Sext, among other things. While I think she deals with mental illness more intense than mine has ever been, her work fixates on themes of love and sex and how they interact with depression and anxiety – so, naturally, I adore her.

Her debut novel, The Pisces, is – as you might already know if you’ve seen any press about it – the story of a woman who falls in love with a merman, and has tons of sex with him. (Yes, a merman, as in a male mermaid. Yes, he lives in the ocean and she lives on land. Yes, he has a dick. It’s under a loincloth.) But at its core, it’s really a novel about love addiction. The protagonist, Lucy, breaks up with her long-term boyfriend at the start of the novel, and falls into a toxic cycle of chasing fantasy men and then being disappointed by them. I found her Tinder tribulations so relatable that I made more Kindle highlights than I’ve ever made in any book, and kept alternately weeping and cackling as I read. “There was something about the morning of a date that tricked me,” Lucy muses, after spending far too much money on lingerie for a tryst that will turn out disastrous-bordering-on-traumatic. “It tricked me out of the haze of being alive. Or perhaps it tricked me out of the sadness of knowing that one day I would die. It punctured the nothingness.” I nodded so hard my teeth chattered.

I saw myself in Lucy’s hapless Tinder dates, and, later, in her pining lovesickness over Theo, the handsome merman she meets near her sister’s beach house. While the novel sets Theo up as potentially being Lucy’s “true love” – the one she’s been waiting for, searching for, longing for – there’s actually no indication that he’s better than any of the online-dating fuckboys who leave her sexually and emotionally dissatisfied. It’s telling that Broder gives her romantically delusional protagonist a dream man who is a literal fantasy creature – and that no other character in the book ever actually sees Theo, so we can’t be entirely sure he exists at all. Isn’t every “true love,” in some sense, a projection, part mirage, a trick of the light?

Far from being the wild merman sex romp it’s been marketed as, The Pisces is a deeply philosophical novel that struggles with huge themes of love, emptiness, and contentment. It spends more time picking apart the whys and hows of romantic addiction than it does describing Theo’s scaly tail or the logistics of his underwater life. We know more about Lucy’s fears, fantasies, and yearnings than we ever know about Theo. But that’s the way of the love addict: making other people into a goal or a punchline, rather than allowing them to just be people.

By the end of the novel, Lucy seems to understand herself a little better, and to have a better handle on what she actually needs. I cried when I finished this book: I cried for Lucy, and for Theo, and for myself. At one point in the story, Lucy quips, “I didn’t want to be seen too closely or I might have to look at me too,” and that’s how The Pisces made me feel: seen, looked at, called out. But ultimately it served as a reminder of the habits I’d hate to fall back into, the fantasies I can no longer rely on, and the emptiness I no longer need to feel.

The Pisces
by Melissa Broder Hardcover
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