dating

5 Rules For Better Online-Dating Interactions

Kate Sloan

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?

Book Review: The Offline Dating Method

Kate Sloan

I receive many press releases per week, and most of them hold zero interest for me. Weird new porn movies. Shitty new vibrators. Swanky events I can’t go to because they’re in New York or Los Angeles.

But recently I got a press release that did pique my interest. It was about a new book that had just been released, The Offline Dating Method: How to Attract a Great Guy in the Real World, by dating coach Camille Virginia.

The concept caught my eye because the realm of “offline dating” advice is usually presided over by male pickup artists. They call it different things – “day game,” “night game,” and so on – but it’s essentially the same idea, just twisted into a different form. PUAs are misogynist manipulators, but this female writer, I gathered, was not advocating the shitty kind of manipulation – maybe just the kind that can get you a date with someone who finds you attractive but who you otherwise never would’ve talked to.

Indeed, while Neil Strauss’s books are guides for men on picking women up, Camille Virginia’s book is a guide for women on getting picked up by men. (Yes, it is painfully heteronormative, so I’m sorry for any accordingly heteronormative statements that follow. Virginia does acknowledge in her introduction that a lot of the tips she offers will work on a broad range of people, not just straight men – and she’s right – but the book is written explicitly through the lens of “You are a woman and you want men to ask you out.”)

Virginia’s central thesis is that meeting potential romantic partners in “the real world” is superior to online dating, for a plethora of reasons: you can make better connections more quickly, and you’ll know much sooner whether you’re actually attracted to and compatible with the person you’re flirting with. In three meaty chapters full of headings and subheadings, she explains how to seem magnetic and approachable, how to start and sustain a conversation with a man you don’t know, and how to transition that conversation into getting asked on a date.

At first, the most striking thing to me about this book was how anathema it seemed to how people my age actually seem to date, and to want to date. I’d recently read an Atlantic article about the so-called “sex recession.” The millennial interviewees spoke about meeting “offline” as an impossibility, an archaic relic, in the wake of Tinder and its cohorts. Take, for example, this sentence where the author, Kate Julian, is chatting with a young female source about Sex and the City: “’Miranda meets Steve at a bar,’ she said, in a tone suggesting that the scenario might as well be out of a Jane Austen novel, for all the relevance it had to her life.” But for all their romanticization of meeting a partner in a bar or a bookstore, these millennials also acknowledge that this type of meet-cute wouldn’t really be welcome in their lives. Julian, who met her husband in an elevator in 2001, writes, “I was fascinated by the extent to which this prompted other women to sigh and say that they’d just love to meet someone that way. And yet quite a few of them suggested that if a random guy started talking to them in an elevator, they would be weirded out. ‘Creeper! Get away from me,’ one woman imagined thinking.”

This is in line with my own experience of dating in a world filled with smartphones and social anxiety. Once, during an extended dry spell in which it felt like I’d never have sex with someone who desired me ever again, I was approached by a random flirty man at a food court while I was reading. After a tense conversation in which I basically politely told him to leave me the hell alone, I tweeted, “Dear men who try to pick me up in food courts: can u not? I’m just tryna eat my General Tao chicken & read my book, bro.” A male friend replied, “Complains about lack of male attention by night, complains about male attention by day” – which enraged me at the time (and still to this day, honestly – hi, Brent), because it implies that all romantic/sexual attention is the same and should be received with the same warmth, whether it’s wanted or not, and that if I ever push back against negative attention, I don’t deserve the positive attention I want.

But as misguided as that feedback was, it also, in some ways, captured the same millennial dating contradiction Julian’s interviewees talked about in her article: we romanticize offline “meet-cutes,” but, at the same time, we find them scary, annoying, or just plain weird.

This is the somewhat hostile context in which Virginia’s writing her book on how to get picked up in public. There’s very little acknowledgment in the book that people might think you’re odd or creepy for trying to talk to them on the subway or at the grocery store – she just says that women are rarely perceived as creepy, and that if someone gives you a weird look for talking to them, they’re not a good match for you anyway and you should just shrug it off and move onto the next person. She does acknowledge that there are certain places and cultures where it might actually be unsafe for a woman to initiate a conversation in public with a man she doesn’t know, but for most women, she seems to think it’s a perfectly normal and acceptable thing to do. I had to suspend my disbelief a little to accept this premise that underlies her entire book, but I’m a socially anxious introvert, so of course I did.

Even if you’re not a straight woman trying to get a straight man to ask for your number, there’s still lots of valuable stuff in this book about general social skills. It contains a lot of practical advice about sparking and maintaining conversations, building confidence, and developing a natural curiosity about your fellow (hu)man. When I read some sections aloud to my extremely extroverted partner, they said all the social tips were fairly obvious to them and almost go without saying, but I didn’t feel that way at all – I think a lot of people who are as socially awkward as me, or moreso, would find these tips illuminating. They give you a blueprint for developing your relational skillset and having meaningful (i.e. not small-talk-y) conversations with people you just met.

So, yes, this is a useful dating book. But I actually found it to be a fascinating read on an entirely different level as well, and here’s where this review gets really weird. As this book picks up steam in the middle, it starts to read like – there’s no other way I can say this – conversation fetish porn.

Hear me out. I’d never heard of a conversation fetish before that phrase popped into my head while reading The Offline Dating Method, but I’m sure it exists. My friend Bex often talks about having a “flirting fetish,” being turned on by witty repartée and double entendres – and that’s what I thought of as I read Camille Virginia’s rapturous magnum opus.

I’m not saying that Virginia necessarily has this fetish, but the way she writes about good conversations is genuinely erotic at times. “You’re going to become addicted to how fulfilling it feels to make other people feel good,” she warns in a section about committing “random acts of kindness” as icebreakers in public. She colorfully defines a “meaningful connection” as “a genuine conversation that feels natural, not forced in any way, and gives each person a feeling of deep fulfillment… being completely present in a conversation and co-creating a shared experience.” After an example conversation in which a man tells her that his cufflinks bear his English family’s coat of arms, Virginia writes, “Boom! You just went from the topic of cufflinks to talking about his family’s 300-year-old estate in Cornwall in less than ten seconds” – profound conversations are as compelling and exciting to her as “number closes” and “kiss closes” are for pick-up artists, and she writes about them with the same slick sensuality. “I’ll admit it: I have an addiction to connection,” she says; “I absolutely love it.”

Virginia talks with reverence about hallmarks of human kinship like sustaining eye contact, making relatable jokes, exchanging compliments, and creating intimacy through authenticity. “Conversations will become an experience that are ten times better than any movie, TV show, or book because you’re not just observing; you’re living the story with another human in real time,” she effuses. “This will not only feel incredibly fulfilling for you but everyone you create that connection with, which means people will naturally want more of you and the good feelings they now associate with you.” She could literally be talking about sex or kink here instead of conversation and the sentiment would still feel true. I’ve never seen someone describe the simple act of dialoguing with such carnal enthusiasm.

I’m not at all saying this to shame her, whether or not this is actually a kink for her, or for anyone else. I actually find it fascinating to observe how eroticizing a particular act, and/or fitting it into a kink framework, can help me look at that act with new eyes and feel invigorated to include it in my life more often. It’s like how thinking of comedians as reaction-soliciting tops has helped me enjoy comedy even more. Understanding that conversations unroll with electric and pleasurable interpersonal energy, just like sex or kink, has made me more jazzed than usual to engage people in conversation, even people I don’t know very well or at all. I enjoy the process more now that I’m specifically chasing the fulfilment and connection Virginia writes about so descriptively (and erotically). I’ve said it before and I’ll say it again: kink is magic.

There are some problematic things about this book, as you might imagine. Safety concerns aren’t acknowledged enough. Every reader is assumed to be a woman who wants to date men but doesn’t want to be so forward as to initiate a date herself. (“Asking a man out myself has never turned out well for me,” Virginia mentions. “I’ve been told by many men that they prefer to ask the woman out and plan the date.”) Most vexingly – and pretty typically, for the dating self-help genre – the author uses herself and her own stories as examples of how easy it is to meet potential dates IRL, without particularly acknowledging that she’s conventionally attractive, thin, white, able-bodied, and socially capable in ways that many people are not. Advice that amounts to “Be yourself!” rings pretty hollow when your self isn’t as traditionally desirable as the advice-giver’s self. I will say that her conversational suggestions don’t necessarily rely on you being attractive, but their positive reception might.

Overall, though, while I went into The Offline Dating Method expecting a light and frothy dating guide that reads like cobbled-together Cosmo tips, it is actually so much more than that. It’s an ode to the beauty of human connection, and a road map to help you get there. It’s a brave stand in a world that has increasingly digitally anesthetized us to our fellow people. It’s also – most surprisingly of all – some of the most explicit and satisfying erotica available for a subculture I’m not sure even exists: conversation fetishists.

 

Thanks to Camille Virginia and co. for supplying me with this book to read!

10 Ways Sex & Hookup Websites Can Be Safer For Women

Kate Sloan

For as much as I talk about dating sites and the hours of amusement they’ve brought me, I don’t actually think they’re that great. They’re too often full of creeps and trolls, seeking to offend and harass more than they’re seeking actual dates or hookups. The situation is dire. Even at times when I’ve been highly motivated to find dates and/or sex on these sites, sometimes I felt cockblocked by my insidious fears about getting catfished or doxxed – or worse, assaulted on a date. It doesn’t have to be this way!

Since so many dating sites and apps are subpar in this area, I’ve put together these 10 suggestions for how these companies can make their services safer and more appealing for women. (A lot of this applies to people other than women as well – anyone vulnerable and/or marginalized, potentially – but I’m a woman so that’s the perspective I’m coming from.) I wish more sites would take these ideas into account!

Comprehensive blocking. I’ve yelled about this before, but… please, please, Hookup Websites, give us a decent blocking feature. You should be able to block someone before you match with them, not just once you’ve already matched (*cough* fuck you Tinder), and once you’ve blocked someone, they should be unable to see any aspect of your profile ever again. This isn’t even that difficult to implement and would make lots of people feel much safer.

A reporting feature that works. If someone is sending unsolicited dick pics, or misogynist screeds, or using pick-up artist tactics, or (god forbid) attacking people on dates, there should be an option to report them on the app or website and have them investigated by a human person (not a robot!) from the platform. If need be, their profile should be pulled. Letting creeps run wild on your site is a surefire way to make women nervous about using it.

Functional filtering. Beyond just making it easier to find compatible dates, this feature can also prevent a lot of scary or annoying situations. I simply don’t want non-feminists to be able to view my profile, let alone interact with me. I’m not saying everyone who rejects the feminist label is dangerous, but certainly in many cases their ideologies are (who the fuck doesn’t want gender equality in this day and age?!), so I just want them gone from my digital life. Nip that “friendly debate” about my personhood in the bud. Byeee.

Identity verification. Okay, this is a controversial one, because some people are understandably skittish about having to upload their ID to a dating site. Some folks even get angry when asked to do so. But I think, provided the data was kept private and managed responsibly (i.e. maybe deleted altogether after verification was complete), it would be worthwhile to make sure people actually are who they’re claiming to be. The internet makes it all too easy to catfish folks, and that’s not cool. Plus I think people would behave better on a platform if they knew it had all their info on file.

Vouching. If you’ve had a good date with someone, maybe you could leave them feedback in the form of a review, like on Yelp, or a rating, like on Uber. Of course, this feature is somewhat objectifying and would likely be abused – I can imagine shitty men leaving bad feedback for women who didn’t “put out” after their date bought them dinner, for example – but it could be useful for shunning creeps.

Taking privacy seriously. I had no idea, for example, when I linked my Instagram account with my Tinder account, that matches and even non-matches would be able to click through to my IG profile and thus immediately learn everything about me; I thought this feature would just show my pictures on my profile. Some dating apps use geolocation, some force you to disclose your school or your workplace, some make you use your real name… All of these “features” are problematic because they put you at risk if someone decides to track you down. Let users decide how much they want to disclose!

Gender self-identification tools. I hear lots of different things from my trans, non-binary, and genderqueer friends about how they wish gender worked on dating sites. However, the common thread seems to be that they wish there were more options rather than less, even if they wouldn’t actually use the options provided. Not every trans woman will feel comfortable disclosing on her profile that she’s trans, for example (especially since doing so often brings on harassment and even violence), but some trans folks prefer to air that stuff upfront so they don’t have to deal with it later. Dating sites should allow for this. In doing so, they’ll also normalize gender disclosure for everyone, not just trans people.

Tools for setting expectations. Many dating sites already have this – but many don’t, and it’s weird! You should always be able to indicate whether you’re looking for something casual, something more serious, either, or something in between. This can help prevent some of the tension that arises when you go on a date with someone whose dating goals end up being different from yours.

Clear community guidelines. I’d rather they be too harsh than too lenient. No unsolicited sexual media, no pick-up tactics, no racism, no sexism, no homophobia, no transphobia, that kind of thing. Setting these boundaries clearly and publicly, and standing by them, would make a company seem more trustworthy to me, and thus more worthy of my patronage.

Investment in sexual health and anti-sexual violence causes. Okay, this one’s more abstract and indirect. But I would definitely trust a hookup platform more if it had made tangible monetary contributions to these causes. Being publicly sex-positive and feminist isn’t just a marketing tactic; it helps establish a culture on the site, and shows abusers and misogynists that they’re not welcome.

What safety features do you wish more dating sites had?

 

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

5 Features I Wish All Dating Apps Had

Kate Sloan

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.

The 5 Essential Elements of a Good DM Slide

Kate Sloan

Ah, the delicate and controversial DM-slide! I remember nodding vigorously when I read Priscilla Pine’s essay “What Comes After Tinder?” and got to the part about Twitter. “Most of the friends I polled who were active Twitter users mentioned it as the app where they had had the most success meeting potential partners, and I know at least one person who eschews dating apps entirely because her DMs have been so fruitful,” Pine wrote (emphasis mine). “In a way, that makes sense: Twitter mimics traditional social interaction in that you can find new people via friends and observe their personalities and senses of humor over time before feeling compelled to proposition them for a date.”

It was a succinct statement of something I already knew to be true: that Twitter was the social platform likeliest to introduce me to new crushes and fan the flames of those feelings, and that Twitter was probably the platform on which I’d be most open to a stranger asking me on a date. Not proportionally, you understand – of 100 people who express interest in me on OkCupid or Tinder, I probably go out with 5 of them, whereas the same calculation on Twitter would be more like 1 out of 300 – but if I develop a Twitter crush, I’m way more motivated to turn our flirtations into an IRL date, if possible, than I am with online-dating randos. I’m already more-or-less sold on them, from consuming their brain in 280-character chunks.

Having met three romantic partners (this guy, this guy, and this guy) and three casual sexual partners (this guy, this guy, and this guy) via Twitter, I’m pretty clear on what I like and what I don’t like, vis-à-vis people sliding into my DMs. Here are 5 elements your next DM convo with a stranger should definitely possess…

Previous rapport. Like Bex says in our Dildorks episode about social media flirting, DMing someone you’ve never actually interacted with before (aside from, maybe, faving their tweets) is like going up to a stranger at a party, tugging them into a closet, and declaring, “I have to talk to you.” They’re probably gonna be freaked out and wonder what the fuck you’re up to.

Establish rapport by adding value to your Twitter crush’s life. Most of my successful DM suitors replied to my tweets with funny jokes, helpful suggestions (when requested), and supportive cheerleading – as relevant – before they dared take things to the next level by DMing me. This is important. When your name and face show up in my inbox, I should recognize them and ideally have a positive association with them from our previous interactions. Hint: if your crush has never faved, replied to, or otherwise acknowledged your public communiqué, they’re probably not interested – or you just need to build rapport for longer before you ramp things up.

A specific reason to message them. Bex recommends following up on a previous conversation the two of you had publicly – e.g. if you and your crush recently commiserated about something sad that happened on your mutual favorite TV show, you could DM them a link to a great article about the show a few days later and say, “Thought you’d like this!” Or you could DM them a link to a local event you think they’d enjoy attending, a thought you had about their latest blog post/podcast/tweet that seems too specific to say in a public tweet, or a thank-you for something they helped you with or introduced you to.

The first time my Sir DMed me, he was following up on a compliment I’d tweeted at him earlier in the day. “Hey Kate! Thanks for that compliment earlier, it made me blush,” he said. “You’re very cute yourself!” This is simple but it worked well because it gave me the opportunity to talk to him more if I wanted to (which I did) or to just say “Thanks!” and move on if I wasn’t interested. Similarly, my first DM from an erstwhile FWB was a response to me tweeting about being sad about the sexual dry spell I was going through at that time: “Sounds like we have similarly sparse dance cards lately,” he said. “Toronto’s been great for work, but surprisingly boring socially.” You’ll notice that this wasn’t a direct date-ask – he left me space to suggest we get together, if I wanted to, which I did – but was nonetheless relevant to our earlier public conversation.

Sometimes your specific reason for messaging them might just be wanting to ask them out. That’s okay, if done well. See “a statement of intent,” below.

An introduction. You might not need to front-load this into your first message if you think your crush is already aware of you and what you do, but it’s nice. Even something as simple as “Hi, I’m [name]! Long-time follower, first-time DMer” could be enough. Introducing yourself is respectful and polite. You probably wouldn’t go up to a stranger at a party and launch into a monologue without at least saying hello and telling them your name, so try the same thing in your Twitter approach.

My Sir did this in his second message to me. “I’m [name], a New York-based [job title]/sex nerd,” he wrote. “Recently found your work and your tweets and it’s all great stuff.” It was a concise statement of who he is, what he does, and why he followed me. Along with his respectful approach, it told me everything I needed to know in order to decide whether I wanted to get to know him better (I did).

A statement of intent. You probably don’t wanna put this in your very first message, because asking someone on a date (or whatever) before establishing rapport is risky, scary, and less likely to work. But if you do decide to ask your Twitter crush to meet up with you, you should give them some sense of what you’re actually asking. Don’t couch your romantic or sexual intentions in a vague request to “pick their brain over coffee” or “talk about [their work].” (And hey, if your intentions are strictly professional, or even casual or platonic, you should find a way to mention that, too. Less confusion = better results for everyone.)

You can straight-up tell them you’d like to take them on a date. You can tell them you’d love to get to know them better over coffee/drinks. You can suggest a specific activity you know the both of you enjoy (e.g. going to a comedy show), ideally one that’s culturally coded as date-y. You can disclose the nature of your feelings about them so they can infer you’re asking them on a date (e.g. “I think you’re really cute and cool and I’d love to take you out sometime” or “I’ve been crushing on you from afar for a while and would love to hang out in person if you’re into that”). My Sir said, “If you’re ever in New York and want to meet a Twitter admirer in person over coffee or something, I’d love that,” which is perfect because it expresses enthusiasm, indicates a specific activity, and gives me an easy out. So many good ways to ask cuties on dates!

Some fucking respect. Twitter isn’t a magical universe where you get to treat people like garbage. Those are real humans in there, so be good to them! Be polite, take “no” for an answer, and be appropriately apologetic if you fuck up.

Make sure you keep in mind, too, that someone ignoring your DM or declining your advances might not have much to do with you. They might be busy, or stressed, or going through a complicated situation of some kind. Don’t take this shit personally, if you can help it. You’re great, and there are always more Twitter crushes in the sea!

Have you ever asked someone out – or been asked out – via Twitter DM? How did it go?