25 Amazing Sexual Experiences I Had At Age 25

Kate Sloan

I’m 26 today, babes! The past few years have been good to me, sex-wise: I got real slutty at age 23, learned a lot about my kinks and relationship style at 24, and settled into a more confident sexual existence at 25. To celebrate this minor milestone, here’s a list of 25 amazing sexual experiences I had while I was 25!

1. Dated a sadist. Despite identifying as a masochist for a few years, it wasn’t until just after my 25th birthday that I started seeing someone who self-identified as a sadist. I got spanked/slapped/scratched a lot in that relationship and it was great!

2. Got tied up. Rope bondage is a trip! I’ve dated two different rope aficionados within the past year, and playing with them showed me that being a rope bottom gets me real subspacey real fast. All that pressure, slowness, and focus puts me into a meditative space that’s unlike almost anything else I’ve experienced.

3. Pegged someone. I didn’t think I would like it, but I did. Innnteresting!

4. Used a blowjob mirror. I’ve been reviewing sex toys for over six years and this was one of the most terrifying toys I’ve tested, though it was also supremely satisfying and fun.

5. Experimented with “forced orgasm” play. I tried this with a few different partners and it typically involved them strapping me down and using a strong vibe on me until I couldn’t help but come. Very fun, would recommend!

6. Demo-bottomed for a spanking workshop. I took my dress off in front of a bunch of strangers and got my ass beat, which was… not as nervewracking as I thought it was gonna be. Maybe I have a teensy exhibitionist streak?

7. Dated a daddy dom. A couple of them, actually. DD/lg has been a fixture of my perv-brain for a few years but this was the first year when I actually tried it with real-life partners, and goddd, I love it.

8. Got a professional erotic massage. And actually had an orgasm from it, which I wasn’t expecting! It happened a few days after a breakup, which made it feel even more healing and necessary.

9. Fucked in an alley. I’d made out in many alleys before. I’d gotten spanked in a couple of alleys. This was the first year I actually had sex in an alley. It was lovely.

10. Had sex in my own place. I moved out of my parents’ house last September, and while I haven’t had a ton of sex in my own bedroom since then (tending, instead, to bang at partners’ houses or a local sex club), it was nice to christen my own space with sexual fluids ASAP. A real adulthood milestone!

11. Went to a sex tradeshow as foreplay. When you and your FWB are both huge sex toy nerds, there are few better pre-sex activities than trawling a tradeshow to see what’s new and hot. I bought a vibe and an impact implement, we flirted and giggled and made bad jokes, and then we had incredible sex at a club. A+ day, 10/10, would do again.

12. Got collared. Collars have been an important kink symbol to me for a long time but I’d never had one that was linked to a specific partner and made me “theirs.” My Sir had never collared anyone before me, either, so it was a super special thing for both of us when he put a collar on me in a Brooklyn hotel room just before we went to see my favorite band and exchanged our first I-love-you’s. So romantic!

13. Tried knifeplay. My pal Dick Wound is a hell of a knife top, so we negotiated some scenes so I could lightly explore my burgeoning interest in knives. It was scary, but in a safe, fun, consensual way. Oh, and a hot way. That, too.

14. Got spanked with a lightsaber. And also a butcher’s cleaver. (Which one would you guess hurt more?)

15. Did educational cam shows. I’ve long offered cam shows of the typically titillating variety, but this year I had a client who genuinely wanted to learn about vulvovaginal anatomy, so I got to patiently demonstrate and explain how I touch myself. Such a fun time!

16. Had a sugar daddy. This was a specific flavor of submission I had never sampled before, and wow, it was exhilarating. Money is so tied up in our personal psychology that I found it was easy to make it sexy, even though I’d never viewed it that way before.

17. Had actually good phone sex. Um, shout-out to people who have a way with dirty talk, because a) I sure don’t, and b) they can make me come really hard. Enough said.

18. Finally had sex with someone after a whole month of only sexting and phone sex. Love a good slow burn, am I right? It turns out you can fuck someone a whole lot better if you have a month’s worth of their sexy communiqué to refer to.

19. Shined a partner’s shoes. I will write about this in more detail when my head stops spinning from the incredible, meditative subspace it put me into. Neither of us had tried bootblacking in any context before, and once we did it together, we knew immediately that we liked it a lot.

20. Played with my wink kink more deliberately. Being winked at, in the right context, has long turned me on, but I’ve rarely had partners who knew how to harness that power to their advantage. My current boyfriend sure does, though. Winking as flirting, winking as foreplay, winking as a hypnotic induction… Woof.

21. Got hypnotized. A whole bunch. Ohhh, it’s so relaxing and hot. I love it.

22. Gave a BJ purely for my own pleasure. This experiment was inspired by my friend Caitlin K. Roberts and a Masters and Johnson concept she taught me about, “sensate focus.” It’s the practice of touching someone else for your own tactile enjoyment, and it can be transformative. I’d never given a blowjob quite like this before, and it really shifted my perspective on oral sex in general!

23. Sucked a dick through a glory hole. Granted, it’s not quite the Full Glory Hole Experience™ if you know exactly whose dick you’re sucking (or at least, I’m sure some purists would argue that), but I was still glad I got to try it. It’s been a fantasy of mine for a long time.

24. Received electrostimulation. I wasn’t sure how I would feel about getting painfully zapped with a Neon Wand, but, like many other forms of kinky pain, it made me subspacey and happy. And I’ll never forget how gleeful I got watching my boyfriend painstakingly try out each attachment on his own arm at various different settings to make sure he knew what he’d be inflicting on me before he did it. Swoon-o-rama.

25. Got “treated for hysteria,” i.e. did a medical-play scene centered around the Victorian notion of “female hysteria” being curable by manual and mechanical clitoral stimulation until “hysterical paroxysm.” The image of my boyfriend in a vaguely doctor-esque white T-shirt telling me, “That’s right, Kate, let go, let it happen” while holding a Doxy to my clit is forever burned into my brain…

What’s the most amazing thing you did when you were 25?

Mini Reviews: We-Vibe Gala, FemmeFunn Ultra Bullet, & Sensuelle Point

Kate Sloan

My “toys to review” pile runneth over at the moment, so I thought I’d bunch a few together… Here are 3 clitoral vibes I have some Opinions about!

We-Vibe Gala (available at SheVibe)

We-Vibe sent me this at my request, because, from the moment I saw it, I desperately wanted it on my clit. It has a two-pronged, bunny-ears-esque shape reminiscent of the Jimmyjane Form 2, which I liked, as a person with a very sensitive clit that can’t handle direct stimulation most of the time. Having the option to surround my clit with vibration, rather than attack it head-on, always piques my interest.

I will say, it’s weird that the famously litigious We-Vibe blatantly ripped off a toy design from Jimmyjane. You would think they’d have picked up some anti-plagiarism scruples at some point while they were suing other companies for stealing their innovative couples’ toy design. But I digress…

I like the Gala’s motor better than the Form 2’s; it’s rumblier and stronger, but not by much. We-Vibe didn’t use their mind-blowing Tango motor in this toy, as far as I can tell, and that seems like a mistake: the sides and shaft of my clit appreciate rumbly vibration even more than the head does. I can get off with this vibe, but it takes a while, and I always reach a point where I’m like, “Seriously? I’m at the highest setting already?”

On the plus side, this vibe optionally pairs with the We-Connect app, so you can control and customize the vibrations more precisely than the toy’s buttons allow for. You can even use the app to create a mode much like my favorite setting on the Form 2, where the vibrations flicked back and forth quickly between the vibe’s two ears, feeling a little like a skilled lover’s tongue. Neat!

Unfortunately, it’s hard for me to take advantage of the Gala’s unique shape because the space between the ears is just slightly too small for my (average-sized) clit, especially as I get more turned on. I was explaining this problem to my boyfriend and said, “I can get it in there if I really kind of, like…” and he supplied, “Jam it in there?” which is exactly the right phrasing. I should not have to jam my genitals into a toy to make it work. It’s not painful, exactly – just slightly uncomfortable and annoying – but that’s enough to put me off using this toy most of the time. This could’ve been fixed by making the space between the ears slightly bigger or by making the ears more flexible. Better luck next time, We-Vibe.

FemmeFunn Ultra Bullet (available at Spectrum Boutique)

I tried this for the first time while on the phone with my boyfriend, and after listening to me using the FemmeFunn bullet and the Sensuelle Point bullet (see below), he correctly observed that I definitely prefer the FemmeFunn. (Dating attentive nerds is fun, y’all.)

I requested this vibe from Spectrum Boutique because my friend Bex had often mentioned it was a surprisingly strong and rumbly bullet for its price point. It’s half the price of the Tango and more-or-less matches it in strength and rumbliness, amazingly. Plus it’s cute as hell: I can’t resist anything turquoise and pink, try as I might.

I don’t like the way it charges: you have to jab the pointy end of a cable through a hole on the base of the toy and blindly hope you’re doing it right and aren’t breaking the toy. Can we do away with toys that charge this way, please, now that it’s 2018 and we have better technologies available to us?

This bullet’s slight flexibility makes it comfortable to use internally, if you don’t mind your penetrative objects being small. However, because the toy bends so easily, it’s also hard to put pressure on my clit with it, so if you like to press vibes into yourself, this might not be the best choice.

I still lean toward my Tango because the FemmeFunn’s squishy silicone makes it conduct vibration slightly less well than the Tango’s hard plastic, and because it’s much more annoying to scroll through the FemmeFunn’s 20 (!) settings than the Tango’s 8. But for its price and its size, this is a remarkably powerful and pleasurable vibe, and definitely my fave of the three highlighted in this post.

Sensuelle Point (available at Spectrum Boutique)

This is resoundingly my least favorite of the bunch, which surprised me, as I’d heard good things about it. It’s a simple, larger-than-standard-size bullet vibe, along the lines of the Tango or the VeDO Bam. However, it’s buzzier than either of those, slightly desensitizing both my clit and my hand after just a couple minutes.

The Point has 20 different speeds and patterns, but they don’t vary much in intensity, so I can’t get the boost in power I need once I’m getting close to orgasm. This toy feels too intense when I begin using it and not intense enough once I’ve been using it for a few minutes. Bummer.

That said, it’s a solidly constructed rechargeable at a reasonable price point ($55) and is made of smooth, luxurious, matte silicone that’s easy to clean. I’d still overall recommend you grab the cheaper-and-better FemmeFunn bullet instead, though, or spend a little more and get a Tango.

Thanks to We-Vibe and Spectrum Boutique for sending me these products to review!

3 D/s Protocols I’m Loving Lately

Kate Sloan
Suz at the Ritual Chamber, photographed by Taylor J Mace

There are many elements of my submission that only come out when a dominant brings them out of me. I only like calling people “Daddy” when there’s someone in my life who has earned that title, for example, and I only fantasize about kneeling to lick the boots of a select few. Dominance and submission are very context-dependent!

That’s why it took me so long to become interested in protocol, I think. I’m defining “protocol” here as a specific set of rules and routines agreed upon by a dominant and a submissive, usually with a particular trigger and outcome: “When [x] happens, you will [y].” I had read about protocol in Sinclair Sexsmith essays and elsewhere, but wasn’t sure it was for me. But when my current dominant partner started discussing it with me, I realized I felt very positively about it – with him, anyway!

Part of the difference, I think, is that we’re long-distance. Protocol is a way for us to feel closer to each other throughout our day-to-day, even though we only get to see each other in-person once every month or two. It’s a way for both of us to confirm to the other that we think about each other often, consider each other in our decision-making, and respect and value the relationship and D/s dynamic we have co-created. Isn’t kink romantic?!

We have several different protocols, all lovingly enumerated in a shared note called “Sir and little one” that syncs to all our various devices, because we’re nerds. Here are three I’m particularly loving lately.

Little one must prepare 3 “interview questions” to ask Sir for every pre-planned (i.e. 3+ hours’ notice) phone call.

This arose from the early days of our relationship, when we learned about each other with ravenous curiosity. He would sometimes teasingly call me out for asking probing follow-up questions aplenty during our conversations. What can I say – I’m a curious weirdo with a J-school education, and when faced with an interesting person, sometimes I go into “reporter mode”!

Asking him questions serves a number of different purposes that make both of us feel good. It makes me feel smart, incisive, and useful. It reinforces our DD/lg dynamic, by making him feel older/wiser and making me feel small/naive. I get to learn more about this person I love, and when he turns the question around on me (which he always does), he gets to learn more about me, too. It deepens our connection in a way that feels really satisfying, which is (IMO) exactly what protocol should do.

The questions are whatever I’m curious about: they’ve been anything from big philosophical queries to small specific ones to sexy ones. I keep an ongoing list of these questions stored up in a Google Doc and move them to an “already asked” list once they’ve been used. Here are some examples, so you can get a sense of what kinds of things I like to ask:

  • “What’s the last thing you did that was really out of character?”
  • “Which friend of yours is the most different from you, and how does that affect your friendship?”
  • “What do you think distinguishes a kinky person from a vanilla person?”
  • “Have you ever stolen anything?”
  • “What are some of your hidden talents?”
  • “Where and when do you get your best ideas?”
  • “What’s your favorite font?”

Sir gets the first taste of all little one’s drinks (excluding water) while they’re together.

My Sir is a cocktail nerd, so when we’re out together, he always chooses my drink and orders it for me. This protocol seemed like a natural extension of that. When he brought it up, he said he wanted to set this rule because a) he always wants to try my drinks anyway, to see what they’re like, and b) he wants to make sure the drinks are good enough for his little girl. Aww.

I like how deferential I feel when this protocol comes into play. Sliding my just-delivered cocktail across the table to Sir for his approval, before I even taste it myself, makes me feel small and powerless compared to him in a way I enjoy.

Protocols involving the control of food or drinks could be triggering for some folks who have struggled with eating disorders, alcoholism, etc. in the past or present, so tread carefully and communicate impeccably if you’re thinking about implementing a protocol in this category. I’m very into ours, though.

Little one must ask Sir permission to come if she’s thinking about or having sex with him, unless he’s going down on her.

Orgasm control is a big kink of my Sir’s, so from our very first sexting and phone-sex sessions, he always wanted me to ask permission before coming. When we wrote up our protocols, we made this rule official.

I was initially very hesitant about this one. My orgasms are sometimes elusive, so when one suddenly felt within reach, I didn’t want to derail it by taking a moment to ask, “May I come, please, Sir?” I worried that if I backed off for even that one moment, I’d screw up my orgasm trajectory and maybe miss out on one altogether. That seemed frustrating and pointless to me.

However, like anything, it’s gotten easier with practice. Now I’m usually able to squeak out my request without losing any headway on the path to orgasm – and I’ve developed enough trust with my Sir to know that he almost always grants me permission pretty quickly. In some ways, this protocol even lessens my preexisting anxieties about taking “too long” to come, because I know I’m not allowed to come without permission and that means my Sir wants to enjoy me wherever I am on the journey to orgasm.

We added the “unless he’s going down on her” caveat recently because my orgasms from oral sex are much more elusive and easily lost than ones I have through other means, so I’d rather focus completely on those without the distraction of having to ask first. There is something hot, too, about oral sex being a “loophole” through which I get to have “freebie” orgasms. It makes me feel even more motivated to relax into those sensations and get off that way.

Bonus: Here’s a protocol we tried that we ended up nixing because it wasn’t working for us:

Little one must show Sir any selfies that she plans to tweet before she tweets them. If she forgets, she must take another photo just for Sir that matches his specifications.

We thought this would be cute because it would make my Sir feel special to get a “preview” of my selfies before the whole internet saw them. I was a little wary, going into this one, that it might make me feel too owned – it felt uncomfortably close to how a monogamous ex of mine demanded I refrain from posting nudes online, even though I wanted to, because he considered that a violation of our monogamy. (That’s a totally fair boundary to set if you both feel great about it. I didn’t.)

However, as it turns out, the owned-ness of this protocol wasn’t what made it hard for me. I have a lot of anxiety about “bugging” my partners by texting them “too much” or at times when they might be busy (say, with another partner), so I found that sometimes, when I wanted to tweet a selfie, the thought of texting my Sir first was too challenging so I just… didn’t. And that meant I was posting fewer selfies and feeling kinda sad about that.

We implemented this protocol for a trial period of 10 days, at the end of which we talked about it to decide whether we wanted to keep it. I was willing to continue with it, but Sir didn’t like that it had become a deterrent to my selfie-posting, so we opted to eliminate it. It served as a good reminder for me (and maybe for you, too) that it’s okay to try protocols out, adapt and shift them as necessary, and sometimes get rid of them altogether. They are never set in stone, and that’s a good thing!

What are your favorite protocols you’ve tried, or wanted to try?

Additional resources on protocol (mostly Sinclair Sexsmith, ’cause I love them):

Behind the Seams: Laughs, Leather, & Layers

Kate Sloan

February 15th, 2018. I wore this to go see PotterProv, the monthly Harry Potter-themed improv show at Comedy Bar, with my friend Zoë. It wasn’t really a thematically appropriate outfit – I mean, unless you think Remus Lupin is a daddy dom – but I had just gotten this shirt in the mail and wanted to wear it out.

I often like to get a li’l dressed up when I go see comedy, because comedians and improvisors are so frequently total babes. Plus I’ve dated enough of them that at comedy venues, there is always a real risk of running into exes or people with whom I went on one or two ill-fated Tinder dates… yikes.

What I’m wearing:
• Hair in little pigtail-knots (I started doing these after seeing Caitlin Roberts wear her hair like this; it’s so cute and easy, especially on days when my hair isn’t cooperating)
• Pink lipstick and pink blush
• Pink pavé Tarina Tarantino heart necklace – eBay, after searchin’ and sleuthin’ and biddin’ for a looong time to find this exact one
• “Daddy” tank top – Redbubble
• Pink bralette – Gap
• Black and white polka-dotted skater skirt – ASOS years ago
• Black leggings – H&M
• Pastel rainbow glitter Doc Martens (!!) – ordered from Urban Outfitters back when these were seemingly unavailable anywhere else in Canada and I NEEDED THEM

February 28th, 2018. Leather jackets always give me so many Gender Feelings! I’ve had this one for years and years and I love its blazer-esque simplicity: it looks equally good over dresses or more boyish outfits like this one. I can’t wait for the weather to get a little warmer here so I can start rocking this jacket every day instead of my winter coat that looks like a literal sleeping bag.

I wore this out to a café to work, and then I dropped by my parents’ place to pick up some sex toys that had been delivered there for me (including the Liberator Axis, oooh!).

My boyfriend told me to put my collar on just before I left my apartment because I had a bunch of writing to do and he wanted me to stay focused. What a sweetheart.

What I’m wearing:
• Danier leather jacket – hand-me-down from an older cousin many years ago
• “Pun Slut” pin from L’Amour-Propre and impact play pin from Kinktionary
• Royal blue suede collar from L’Amour-Propre
• Bright yellow Goodbye Honolulu T-shirt – a gift from Max
• Black jeans (a rarity – I loathe wearing pants)! – Gap
• Black leather Frye harness boots
• Ye olde giant black nerd glasses – Hakim Optical
• Heart-eyes emoji phone case – Redbubble

March 16th, 2018. The first time my love came to visit me in Toronto, he gave me specific clothing instructions: I was supposed to wear an outfit that would be fun for him to take off me, like unwrapping a present. Now that’s a femme challenge that I’m absolutely up to!

I chose this ensemble lovingly in the days leading up to his arrival, and laid it out on a chair in my bedroom the night before. When I woke up that day, I finished up my morning dayjob work and then slipped into this outfit slowly, methodically, very aware as I slid into each layer that my beautiful boyfriend would be removing it from me in reverse order in just a couple hours. And he did, and it was lovely.

What I’m wearing:
• Blue and black heart-print cardigan – H&M many years ago (I’ve had this since at least 2007!)
• Pink lace slip – vintage via Coldfish on Etsy
• Navy high-waisted A-line skirt – Old Navy years ago (I used to wear this a lot when I wanted to look businessy in journalism school)
• Pink and navy kneesocks – no idea, but they’re cute, eh?
• (Unseen) Pink and purple polka-dotted panties which I later gave to my boyfriend as a gift because he did such a good job getting them wet while I wore them – La Senza, I believe

What’s your favorite outfit you’ve worn recently?

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?