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!
What’s the best piece of advice anyone ever gave you about [romance/business/creativity]?
What song or album are you obsessing over right now?
What’s your favorite memory from childhood?
What’s your go-to comfort food?
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?
Who is the most famous person you have met?
What’s an outfit you feel amazing in and why?
What’s the best thing you know how to cook or bake, and how did you learn to make it?
What’s a movie you wouldn’t necessarily say is your all-time favorite, but that you love nonetheless?
What’s a weird inside joke you have with a friend and how did it start?
What’s a common misconception about your job?
What was the last book you read, and did you enjoy it?
Do you feel like you’ve found your “life purpose” yet?
What country would you like to move to if you had the chance?
When was the last time you did something that made you nervous?
Did you have any weird hobbies when you were a kid?
What’s your morning routine?
What’s your favorite holiday?
What is the wildest lie you’ve ever told?
What’s your favorite scent?
Who would you consider a hero of yours and why?
What do you keep on your nightstand?
Are you an introvert or an extrovert?
What part of your body do you like the most?
Who was your favorite teacher in school and why?
What would you do with your time if capitalism was abolished?
What’s your favorite word?
What role does social media play in your life, and how do you feel about that?
What’s your favorite thing about your home?
What celebrity do you think would make a really great roommate?
Which fictional character do you most identify with and why?
What’s a piece of media that can reliably make you cry?
What’s a task most people don’t like doing that you actually enjoy?
What do you think will be the biggest technological innovation in our lifetimes?
If you were famous, what would you want to be famous for?
What’s an item of clothing you wish you owned?
What makes your best friend so terrific?
What’s the last problem you solved?
What’s one of your hidden talents?
What’s the most athletic thing you’ve ever done?
What’s a social rule or expectation you totally ignore?
What’s the most common compliment you receive?
What’s the best kiss you’ve ever had?
If you were going to start a podcast, what would it be about?
What’s an out-of-character decision you’ve made recently?
What’s the best Halloween costume you’ve ever worn?
What’s something you love, without really knowing why you love it so much?
What’s a bad habit you’re trying to break?
What’s the fanciest event you’ve ever been to, and what did you wear?
What question do you wish more people would ask you?
Hanging out with Jaymz Bee at a jazz loft party in 2015.
Content note: This post will touch on social anxiety, alcohol, and drugs.
Parties are simultaneously the bane of my existence and some of my most looked-forward-to events. I’m sure some of the introverts reading this can relate! I love the getting-ready part and the chatting-tipsily-with-cool-people part; it’s the part in between that usually makes me nervous – sometimes to the point of not wanting to attend at all! If this sounds familiar, don’t worry: I’ve got some tips to help you get through the next party you attend. Here we go…
Wear at least one “conversation piece.”
Getting ready for a party feels to me like casting a magic spell. It sets the tone for the whole event and lays the groundwork for how I will feel, and how I will be perceived. One thing I always try to do when assembling a party ensemble is to include clothing items and accessories that are eye-catching, a little odd, and easy for someone to comment on or ask about. As you probably know, one of the trickiest things about approaching new people at a party is not knowing what to say – so by wearing something worth remarking upon, you’re doing the other party-goers a favor by giving them a free conversation starter to use with you! Some of my fave eye-poppin’ pieces are flashy heart-shaped jewelry, oversized hair accessories, enamel pins, bright-colored lipstick, and really great shoes.
Tell yourself you only have to stay for an hour.
I do this for almost every party I ever go to, and in almost every case, I end up staying longer than that one hour. It’s just a way of tricking my brain into letting me attend the party, because I know I can get through an hour, even if the whole hour sucks (which it never does). This is also a way I take care of myself: if I genuinely want to leave after an hour, it’s almost certainly because either the party is bad or there is something going on with my physical or mental health that’s making it difficult for me to enjoy myself – and in either case, I’d be happier at home on the couch, wrapped in a blanket and watching Netflix. If you’re attending a party with other people, you might want to tell them about your time-limit plan, too – this is a way of setting expectations so you don’t disappoint your party-animal friends when you’re walking out the door while their night’s just getting started. (Remember: even if you live together, you don’t have to leave the party at the same time!)
Keep your eyes up and your body language open.
I went to a raucous party full of mostly strangers with my partner last week (more on that soon) and noticed that way more people came up and talked to us than would ever approach me if I’d been there by myself. Setting aside the fact that my partner is very handsome and magnetic (which they are), I think this phenomenon mostly occurred because my energy was totally different than it would’ve been if I was alone. I wasn’t hunched over my phone in a corner, or affecting faux-blasé body language to seem cool and aloof – I was looking around the room, bright-eyed and phoneless, curious about who we could talk to next. Of course people wanted to meet us! Consider adapting the way you hold yourself, behave, and look at folks the next time you attend a party – it could totally transform your experience.
Come up with a go-to line to start a conversation.
Asking someone how they know the host is usually a safe bet. Complimenting some aspect of their outfit, as we’ve discussed, is another. If a holiday is coming up or has just passed, you can ask someone how they spent it or plan to spend it. Dating coach Camille Virginia recommends commenting on something in your environment – like, “Wow, this playlist is incredible,” or “[The host] always throws such great parties.” If you’re feeling a little braver, you could also just ask people one of these 100 questions Alex Franzen recommends – they might think you’re a bit of a weirdo at first, but then they’ll probably be excited to answer such an interesting question!
Watch your alcohol/drugs intake.
Look, I’m not going to tell you how to live your life; I’m not your dad. I just know that when I feel anxious at a party, I often lean too hard on substances, both to alleviate my mental discomfort and to give me something to do with my hands so I feel less awkward. If I get too drunk or too high, I almost invariably end up doing something I regret – often something embarrassing enough to give me even more anxiety the next day when I remember what happened! Naturally, this topic is extra fraught for people who struggle with addiction, or have done so in the past: parties can be a very triggering or challenging environment. When I’m trying to lay off the substances at a party, I’ll usually pour a non-alcoholic beverage (or even just water) into my glass and sip on that, or nibble on a snack – both help me feel less out-of-place and awkward, without getting me wasted.
Find one person and make them feel fascinating.
One of the reasons parties stress me out is that I feel a pressure to talk to tons of people – but the truth is, I often have my best party-going experiences when I only have one or two intense, intimate conversations, as opposed to several more casual or perfunctory ones. This jives with what some social psychology thinkers say about how introverts hate small talk and much prefer more soul-baring interactions. If you can find even just one person at the party who has an interesting job, or majored in something cool, or has an amazing outfit on, or is obsessed with the same TV show as you, you can ask a zillion follow-up questions (so long as they seem up for that) and go deep with this one person instead of swimming around in the shallow end with a bunch of people you barely know.
Take breaks when you need to.
Remember what I said earlier about how you should keep your phone tucked away and your eyes up? Yeahhh, there’s only so long I can do that for. Most of my introverted friends have some sort of system for taking periodic breaks at parties, whether they like to head outside for a smoke, step out on the balcony for a quiet moment alone, or hole up in the bathroom to check their email (just be mindful that other guests might need to pee!). At particularly crowded parties, sometimes you can take a time-out just by sitting in the corner by yourself and texting a friend or reading an article on your phone. (I used to have a friend who would legit bring a book to every party and unabashedly pull it out to read when she needed a moment of simulated solitude… Kudos.) You might find your brain feels more juiced up and socially energetic after even a brief breather, so you can get back in there and keep the party going.
Help with party logistics if you can.
Ask the host if you can help make drinks, collect used dishes, take people’s coats, run the evening’s game of Charades, or whatever other practical things need doing. This’ll help you feel less awkwardly aimless, while also giving you a low-pressure opportunity to meet and talk to a lot of the other attendees. Plus you’ll be helping out the host, who is probably rushed off their feet!
See someone standing alone? Go talk to them.
They’re probably one of your own kind! And they’ll almost certainly be grateful you bothered. A simple “Hey! How’s your night going?” can turn someone’s whole evening around. Similarly, if you’re standing in a group and you see one or two people nearby looking left out, invite them into your circle. Parties are supposed to be all about mingling, after all!
Exit conversations gracefully.
I’m not always the best at this. Sometimes you want to leave an interaction, either because you’re getting socially overwhelmed or you just… don’t really like the person you’re talking to. It’s possible to do this without seeming rude, but most people aren’t very good at it! Try one of these lines: “Well, it was nice talking to you. I’m gonna mill around.” “It was so good to meet you – have a good time tonight!” You could also just make up an excuse (“I have to go to the bathroom,” “I have to go help my friend with something,” “I have to make a phone call”) but the truth is better, and often kinder.
Recharge as needed when you get home.
You probably know what kinds of activities help you reset your brain after expending a lot of social energy. I like to get in a hot bath with a book, watch some silly YouTube videos, or just stare mindlessly at my phone for a while. Whatever works best for you, do it – not only because you need it, but also because you’ll start to associate parties with that horrible drained feeling if you let yourself linger in that mood for too long after a party. Doing proper post-event self-care helps keep your relationship to parties a positive one!
What are your best tips for going to parties as a shy, anxious, and/or introverted person?
Earlier this year, the New York Times wrote about 36 questions that strangers can supposedly ask each other, which will make them fall in love real quick. You alternate asking each other the questions until you’ve gone through all 36, and then you stare into each other’s eyes silently for four whole minutes. By the end of this process, you’re sure to feel more connected to the other person, if not full-on in love.
I was reminded of this article when I last went to Body Pride, because, in the midst of sharing all these intimate emotional details with one another, I started to feel like I was… kinda falling in love.
Those feelings haven’t particularly persevered, but then again, those aren’t people that I see very regularly. I think that if you developed a crush because of the deep and sudden intimacy fostered in environments like Body Pride, and then you kept spending time with the person on a semi-regular basis, those initial crush-y feelings would inevitably develop into something deeper.
My questions are different from the ones suggested in the NYT article, but they have the same aim. I think if you asked someone these questions, and really listened to their answers, some kind of magic would happen.
1. What are you passionate about?
I can’t imagine a sexier quality than enthusiasm. Everyone reaches their peak cuteness when they’re talking about something they find fascinating and exciting. It doesn’t matter if it’s fashion, photography, blogging, bowling, triathlons, trigonometry, web design or witchcraft: if it turns their crank, then watching them talk about it will be a delight.
True, a relationship might not have long-term legs if the other person’s passion bores you. But if you can’t get excited about the topic of their tirade, you can at least get excited about the way their eyes light up and a smile blooms across their face while they ramble at you about fancy stationery or rock operas or whatever.
2. What are you insecure about?
As a culture, we’re obsessed with the notion that confidence is attractive. And it’s true, it is. But that doesn’t mean insecurity is always a turn-off.
In fact, talking frankly about your insecurities requires confidence, or at least bravery. Whining about your least favorite body parts isn’t hot; projecting your own shit onto other people isn’t hot; refusing to take any risks in life because you hate yourself isn’t hot – but owning up to your issues? That’s hot. Especially if owning up to them makes you decide to actually do something about them.
In my life, I’ve only had maybe two or three really open, honest conversations with people about our mutual insecurities. And far from whiny or boring, it was revelatory. There is something incredibly powerful, for your own self-image and for your relationship, about discovering that other people have the same bullshit negative self-talk that you do. Like the NYT article says: “mutual vulnerability fosters closeness.”
3. What was the last thing that made you laugh really, really hard?
Occasionally someone will try to tell you a story or a joke, but they’ll start laughing so hard that they can’t even finish a sentence. Their face goes red, their voice gets hoarse, maybe some tears stream down their cheeks. They keep going back to the beginning of the sentence to try and get through it, but they just can’t, and it’s hilarious.
It’s also fucking adorable.
We all spend most of our time fairly stoic, moving through the world in a calm and orderly way, even if we’re total freaks and weirdos underneath. When you meet a new beau, it might take several dates – or even several months – before you really break through that crust of composure and get to the kooky good stuff underneath.
But if you ask them about the last time they laughed so hard they couldn’t breathe, and then they tell you that story… you’ll get a little preview of their zaniness. A glimpse of how it looks when they let loose, lose control, lose their shit. And that’s cute as fuck.
