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The Good, the Bad, and the Awkward: 5 First Dates I’ll Never Forget

Kate Sloan

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Dating is so weird. It simultaneously triggers my anxiety and makes life seem beautiful. It’s an antiquated practice but still feels fresh and crucial. Good dates can be amazingly, astonishingly good, and bad dates can be unendingly, unforgettably bad.

Dating and hookup sites like Justlocalsex.com make it easy to find dates plentifully and quickly, but after a while, sometimes all those trepidatious evenings start to blur together. There are, however, some dates I’ve been on that I will just never, ever forget. Whether memorably marvelous or memorably mortifying, here are five dates that will stick in my head forever…

My first date ever was with a boy I met on DeviantArt (ugh, god, I know!). A high schooler already, he seemed devastatingly wise and cool to my dweeby middle-schooler ass. We met ostensibly to trade photography tips and wander around Kensington Market taking pictures, but first we made a pit stop in a nearby Burger King to fuel up for our mission.

It’s normal for conversation to be stilted when you first meet someone in person, as you both shake off first-date jitters and get to know each other’s conversational rhythms. But sometimes that rigidness just doesn’t go away. This was one of those dates.

After waiting in line to buy our food and finding we had damn near nothing to say to each other, we sat down with our burgers and fries and tried not to look each other in the eyes. Mid-bite, he shook his head sadly and proclaimed, “This is exactly the kind of awkwardness I was hoping to avoid.”

Needless to say, there was not a second date. I think he later came out as gay – which might explain our lack of romantic or sexual chemistry, but not our lack of conversational chemistry. Dates can still be great even if they end up veering less romantic than expected – I’ve made some of my closest friends that way – but that was not the case here. It was, shall we say, not an auspicious start to my dating career.

2267570972_b6771af296_oMy first good date was with a gorgeous, goofy, purple-haired lesbian I’d had a crush on forever. The week previous, I’d confessed my feelings in a handwritten note containing lovelorn excerpts from my journal. My crush was reciprocated, and now, tentatively, she was my girlfriend and I was hers. It was the most exciting and terrifying thing that had ever happened in all my fifteen years on earth.

We met at her favorite coffee shop, Chocolate Heaven. My cafés of choice at the time were Starbucks and Tim Hortons, so this cozy indie haunt seemed as refreshingly quirky as my new girlfriend herself. She ordered a cappuccino and I swooned; what a cool thing to drink, I thought. I ordered a hot chocolate and my hands shook so much, the mug clattered in the saucer.

We talked for hours. We couldn’t stop talking. Her synapses fired so quick, it was like riding a roller coaster of puns, anecdotes and retorts. Her eyes flashed brightly, her hands swirled in wild gesticulations, and she spun clever yarns I devoured with fervor.

When we couldn’t reasonably linger in the café any longer, I walked her home. On her porch, I rocked back and forth on my heels, shoved my hands in my pockets, hemmed and hawed. I’d never received a kiss; how could I be so bold as to initiate one? But somehow I did. I leaned in, and – ouch – our foreheads collided. We tried again. My nose crashed into hers. “One more time,” she giggled, and we gave it another shot. That time, it worked. I skipped home like the smitten idiot I absolutely was.

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One night in 2009, a boy rang my doorbell. I answered the door with tears in my eyes. He was the reason I was crying, and he knew it. He’d betrayed my trust, and I was crushed, in more ways than one.

I said his name when I opened the door, surprised to see him. “I really like you,” he blurted in response. This was new information to me. “Would you maybe wanna go out with me sometime?”

“Let me get my coat,” I managed to respond, the tears already drying on my cheeks.

We went to a nearby café. I ordered a chai latte, which he insisted on paying for, in that dorkily chivalrous way teenage boys have. As we waited for our drinks at the bar, I chirped, “I can’t wait to call my best friend and tell her I went on a date with you! She’s gonna freak out.” He grinned and replied, “Why don’t you call her right now?” He was a weirdo. It’s one of the reasons I liked him so much. I took my phone out of my pocket and dialed, unable to stop smiling.

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My most life-changing date was in March 2011, and I didn’t even want to go. It was my first time meeting an OkCupid suitor in person, and I was nervous about any and all possibilities: nervous our conversation would be awkward, nervous he’d think I was ugly, nervous he’d be an axe murderer. I asked my best friend to casually “drop by” the tea shop where the date would take place, about midway through, so she could save me if I needed saving.

As it turned out, I had no reason to worry. I showed up and found that the boy was charming, smart, witty, and kind. We geeked out over Pokémon, bemoaned the shortcomings of OkCupid, and laughed at each other’s weird jokes. When my friend stopped by to check on me, I told my date that she was doing this and why, and he was completely cool with it. He understood. We bid my friend adieu and my new cutie walked me to my doorstep.

We didn’t even kiss on that first date, and that is why I will argue ceaselessly with anyone who claims a first date has to end with a kiss or the match was a failure. That man ended up becoming my first serious boyfriend, my first love, and my portal into new worlds. We took things very, very slowly, and I’m glad. That first date was just as effortlessly delightful as the rest of the relationship. I don’t regret a bit of it.

tumblr_nnsjpdxtr61qzigipo5_1280My first Tinder date was with a cute comedian. I met up with him at a sketch show, breathless and late. “What did you do today?” he asked, conversationally. “Oh, I was working on a post for my blog,” I told him. “What was the post about?” he asked, and I had no choice but to tell the truth: “Um, it was about my clit.” He reacted, I should say, admirably well.

The show was so funny I repeatedly choked on my beer. Afterward, I asked, “Do you wanna hang out for a while?” and he said, “Yeah, I really do.”

We sat in the dim scuzz of Comedy Bar for hours, asking each other questions about our childhoods and favorite movies and online dating experiences. Eventually we meandered to McDonald’s for some food. I remember he complimented my blue tights and asked if he could touch them. I think that was the moment I decided I wanted to have sex with him. And later, I did.

It’s funny how, even though that relationship ended terribly, the first date still shines in my memory. Sometimes a first date is a preview of the magic to come, and sometimes it’s the only magic the two of you will ever conjure together. Either way, good first dates are worth appreciating: they are preciously rare in this world.

What are the most memorable first dates you’ve been on?

 

Heads up: this post was sponsored, but as always, all writing and opinions are my own!

“Every Feminist’s Ideal Boyfriend…”

Kate Sloan

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During the shitstorm of anti-feminist trolls I faced after the publication of my Establishment article, the funniest criticism I received was this: “Every feminist’s ideal boyfriend is a Hitachi Magic Wand.”

A conservative blogger had written about me and my degenerate sex toy collection, and I clicked the link while at a party with a bunch of friends. When a concerned pal saw what I was reading, he cooed, “Aw, don’t look at that,” and tried to take my phone from me so it wouldn’t ruin my night. But I wasn’t sad or angry; I was giggling my ass off.

It struck me (and still strikes me) as so funny that these anti-feminist, anti-woman, anti-pleasure curmudgeons think sex toys are incompatible with the presence of a real-life partner. These people honestly believe that by sheer virtue of owning dozens of vibrators and dildos, I am scaring away anyone who might want to bang me. This couldn’t be further from the truth.

I’m throwing clothes and toiletries into a backpack, getting ready for a weekend at my boyfriend’s place. It’s a rarity: he has the house to himself, with his family being out of town. We are going to fuck on every available surface.

My eyes land on my sex toy drawers and I realize some important decisions need to be made. “What toys should I bring?” I text my love. While waiting for him to respond, I idly graze my fingers over my Tango, Orchid, and Wahl.

The reply comes back: “Your Eroscillator. Duh.”

I should have known. He loves how hard that toy makes me come, while his cock is deep inside me or his fingers probe my G-spot. Sometimes he even hands it to me during sex without me needing to ask – a non-verbal assertion that, yes, he values my pleasure, it’s important to him, it turns him on, and he can’t wait to feel me clenching around him.

I wrap the Eroscillator’s cord carefully around its body and slide it into my bag, then skip off toward the subway station.

27 percent of the people I’ve banged have owned their own Magic Wand (to my knowledge, anyway). That’s no small number. That’s 1.3 in 5. Those odds are pretty good, compared to the world at large. I have excellent taste in partners.

Though self-pleasure is obviously an important ideal to me, I’m especially charmed by cis men who own a Magic Wand purely for the usage of the women they bone.

These are usually men to whom their partners’ pleasure matters a great deal. They’re the type of men who want you to come, but who will back the fuck off if you tell them it’s probably not gonna happen tonight and you’re okay with that. The type of men who will patiently offer up their fingers, mouths, dicks, and talented toy-wielding hands if it means they get to watch you writhe and convulse beneath them. The type of men who will never judge you for getting sweaty, red-faced, breathless, loud, and incoherent during and after your orgasm, because to them, that’s not unattractive – it’s the whole point.

When I’m flirting with someone new and sex toys come up in conversation, sometimes I learn that my flirtee owns their own Hitachi. It’s usually mentioned so casually and offhandedly, I could miss it if I zoned out for just a moment. But it’s info that perks my ears right up, because I know what it’s likely to mean.

“I bought it for an ex-girlfriend, but she didn’t want it,” he says with a shrug as he plugs it in.

“Lucky for me,” I fire back, unwrapping a condom to pull over the thing’s unwieldy, porous head.

I’m already wet from his deft fingers, so he can push them right into me again once the Hitachi is settled on my clit. I turn it on just as he finds my A-spot and have to bite down on my own hand to keep my moans at a reasonable decibel level. The deep vibrations rocking my entire clit combine with his sweetly insistent fingers, and I zoom right into “about to come” territory within seconds.

It doesn’t take much. I’m just thinking that I wish he would say something nurturing and domly to me to push me over the edge, when he leans in and mutters, “Does that feel good? Yeah? Like that?” And then I’m coming all over his fingers, sinking my teeth even deeper into my own skin. The vibrator rattles noisily against my sudden wetness and I leave it there until I can’t stand it anymore.

“Man, I love that thing,” I breathe. He laughs and says, “Yeah, I could tell.” We curl up to sleep: him spooning me, and me spooning the Hitachi.

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The way I use sex toys with partners, it’s a way they can prove to me that they trust and respect my authority over my own body.

I rarely just hand a partner a toy and let ’em go wild with it. Usually I’ll hand it to them while listing some very specific instructions. “Push it all the way into me, tilt the tip up toward my belly, and move in and out in small motions. Yeah, like that. A little bit faster, please.”

Or sometimes I’ll just hold the damn thing myself. I’ll press a vibrator against my clit or external G-spot while my partner fucks me with fingers, a toy, or his dick. Since my clit is a total princess, it’s often easier if I handle that part myself, freeing him up to do other things.

I don’t attract the type of person who’d pridefully try to control my toys against my wishes. I wouldn’t want to bang that type of person, anyway. I only want to be with people who respect my autonomy, my knowledge of my own body, my pleasure preferences. And when a partner hands me a vibe without getting butthurt about it, without sulking in disappointment, without seeming to feel devalued or unneeded, it just proves he trusts me to know what’s best for me.

It’s a feminist act, in some ways. It’s a man saying-without-saying, “Your body is yours, you’re smart and experienced, and your pleasure matters. I’d love to be a part of that, if you’ll let me. And if not, that’s fine too.”

He’s got one hand on my chest and the other inside me. My Tango is wedged against my clit, thrumming helpfully, but I’m just not quite getting there.

I see a look come over his face that I can’t decipher, and then he says, “I don’t think this is strong enough. Do you wanna switch to the Hitachi?”

My appreciation for this man, in this moment, is grander than I can translate into words. My heart melts, and so does my vagina. Far from being scared or put off by vibrators, he’s getting annoyed with the one in my hand for being too small, not strong enough, not giving me enough pleasure. He wants more for me, because my enjoyment is paramount to him. And not in some selfless, detached way: me getting off is a direct turn-on for him. And I know that’s why he shuts off my Tango, retrieves my Magic Wand from the bedside table, and places it in my hands.

A few diligent minutes later, I come so hard that I’m babbling, sweating, lost in rumbly reverie. I’m vaguely aware that he takes the vibe from me once I’m totally done coming, and I hear him set it on the table before climbing back into bed with me.

Maybe it’s the orgasmic neurotransmitters talking, but I’ve rarely felt so cared for, respected, safe, and seen during sex as I do now. He knew what I needed and delivered it not with complaints but with extreme enthusiasm. It wasn’t even a big deal to him. He wanted me to come, so, duh, he made sure there was a suitable vibrator in my hands. It was the obvious thing to do, and he did it because he cares about me.

I drift off to sleep in his arms. His hands still smell like me.

What’s in a Name?

Kate Sloan

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“What do you want?”

He’s got me backed up against a fence, in one of the many residential alleys that crisscross through the Annex. The fence is painted bright turquoise, and it must make a beautiful backdrop for this foreground: a pale and blushing babe in a blue dress. Me.

His hand is on my ass. He knows what I want, but he’s still gonna make me say it. “I want you to spank me, sir,” I choke out, his lips so close to mine that he must feel my words as much as he hears them.

He chuckles. I can tell he likes it when I call him that. “I don’t have a name for you yet,” he replies, like this only just occurred to him.

I am more than prepared for this eventuality. “I like to be ‘princess,’ or ‘little one,’ or ‘babygirl,'” I list off. These names are well-traversed in my life, but they still feel fresh and important. They’re heavy on my tongue and hot in my ears.

“Okay, princess,” he says with a dark smile. “You gonna be a good girl for me?”

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“Princess” was my first kink honorific, the first name I remember loving being called. A dominant fuckbuddy casually mentioned it one day while we were discussing my burgeoning DD/lg kink. It felt right to me when he said it, in the same way it felt right when I discovered other words that describe me, like “femme,” “queer,” and “submissive.” I sexually identify as a princess.

Not a literal princess, you understand. I don’t have a kingdom to rule over, royal subjects, a family of other monarchs. I am a princess in the way that Veruca Salt and Angelica Pickles are princesses: a treasured and perhaps slightly spoiled little girl whose daddy unflinchingly loves her and dotes on her. A dainty little thing, with a bratty streak that comes out when provoked or challenged. A precious but ultimately powerless little gem of a person, revered but not really respected. I’m that kind of princess.

Though I’m enamored with the “Daddy Dom/little girl” dynamic, I almost never call partners “daddy.” It feels wrong to me, and not just because it’s taboo. I’ve never used that word with my actual dad either; it feels babyish and saccharine in a way I don’t particularly enjoy. I don’t say that to shame anybody’s kinks; if you like that word, that’s fine and good for you! But for myself, I gravitate more toward “sir.” It communicates what I want it to, without making me cringe. And, if I’m honest, calling partners that makes me suuuuuper wet.

“Little one” was introduced to me by the aforementioned dom fuckbuddy, too. He dropped it into our dialogue mid-fuck one day and my reaction far surpassed what I could have predicted. He was the exact same height as me, probably even weighed less than me, and yet, with those two simple words, he made me feel inescapably smaller than him. Diminutive and defenseless. A mere insect under his boot heel.

My relationship with this title is fraught with guilt, because I worry it’s related to patriarchal size-shaming. I’m a chubby lady so maybe it makes me feel better – sexier – to be literally told that I am small. But I don’t think that’s the whole story. Smallness is associated with traditional femininity, sure, but it’s also connected to powerlessness, a state of being that I eroticize deeply. When someone calls me “little one” and I get wetter and hotter, I think it’s more about the condescension and coddling than the physical littleness being evoked.

“Babygirl” is more ambiguous. Vanilla partners call me “baby” sometimes; it’s a common epithet, in this world of Biebers and Backstreet Boys. But there’s patriarchy baked right into it: this name infantilizes its subject in the most literal sense. My inner feminist struggles to accept my affinity for being called patronizing names. My inner sex-positive feminist, however, knows it’s okay for me to like whatever I like, as long as I don’t replicate those power injustices in my actual life.

Names, labels, identities: these things are important, regardless of what the “Labels don’t matter!” crowd says. Labels help us organize ourselves, understand ourselves, understand who we’re attracted to and what we want. Not to mention, they can be really fucking hot.

One night I was at a party, and several people were sporting tiaras. A domly friend of mine made a paper crown for Bex, since their gender identity isn’t always tiara-friendly. “How is the king?” he asked Bex later, when their makeshift crown was atop their head. And then, looking at me: “And the queen?”

“She’s not a queen, she’s a princess,” Bex retorted, before I could even respond. And they were right.

“A Casual Fuck Can Only Bring Bad Luck…”

Kate Sloan

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I’ve gotten better at casual sex in the past year. “Better,” you understand, but still not “good.” When I fuck someone, however casually, I still tend to Google them afterward. Maybe creep their Facebook photos a bit. Tell all my friends how cute they are. And then, usually, I’m done obsessing and can move on with my damn life.

But I didn’t always have that ability. I wrote this song, “Casual,” a year ago, when I was struggling with a crush on someone who only wanted to see me occasionally and only between the sheets. It was a major adjustment for my brain to learn that sex and romance don’t always have to be connected. And in the interim before I figured that out, I was sad for a while.

I hope you like the song! The lyrics are below for you to read. If you want to keep this song while also supporting me, you can buy it on Bandcamp and it’ll be yours forever, so you can listen to it on loop while crying over your unrequited love… Er, I mean, so you can listen to it while going about your totally normal, emotionally well-adjusted life. Yep.

“Let’s keep things casual,” you said
My heart exploded cold with dread
I don’t have the strength
To keep you at arm’s length
I fall for all callers to my bed

A casual fuck can only bring bad luck
‘Cause I’ll end up stuck on you
For no-strings-attached, we’re so badly matched
And I’ve got a crush on you

Give me some credit, if you please
I’ve put all my feelings in deep freeze
This isn’t romance
It’s not my one big chance
It’s just a blowjob on my knees

A casual fuck can only bring bad luck
‘Cause I’ll end up stuck on you
For no-strings-attached, we’re so badly matched
And I’ve got a crush on you

We still stay perfectly polite
But we never got this thing quite right
It makes me feel dumb
That you can make me come
But I can’t even make you stay the night

A casual fuck can only bring bad luck
‘Cause I’ll end up stuck on you
For no-strings-attached, we’re so badly matched
And I’ve got a crush on you

5 Awkward But Effective Ways I’ve Initiated Sex

Kate Sloan

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Being a sex blogger, contrary to popular belief, isn’t all sensual sweet nothings and longing looks all the time. My approach to sex has never been what I would call “sexy.” I am, instead, a dorky goofball in the sack. And fortunately, that’s worked out pretty well for me.

I don’t know how “normal people” initiate sex. Maybe there’s no such thing as “normal people” when it comes to sexuality. There’s only what’s common, and what’s less common – and I’d wager that awkwardness in bed is far more common than most folks would admit.

Below are five actual things I’ve said in an attempt to get the sexy ball rolling. These are all lines that worked, i.e. happy and enthusiastic sex resulted soon thereafter. I share these not so much as prescriptive suggestions, but as a reminder that you can be silly and strange in bed and still be sexually successful (whatever that means to you). If you’re a weirdo and someone is excited to bang you, that excitement is partially because you’re a weirdo, I promise. Own that, use it, and don’t be ashamed of it!

“I kinda wanna cuddle you. Would that be weird?”

A lot of my sexual initiations begin with “I kinda wanna,” actually. It’s less anxiety-provoking for me than a cocksure proclamation of intent, but it still communicates desire. “Would that be weird?” is really just another way of asking “Would that be okay?” or “How would you feel about that?” – a.k.a. requesting consent.

I said this while lying in bed talking with someone who I found intensely attractive but whose feelings about me I wasn’t sure of. I wanted to do much more than cuddle him (and eventually we did), but I figured this request would be a gentle way to test the waters. He laughed and said, “No, that wouldn’t be weird!” and I breathed a sigh of relief as he pulled me in toward him, because I had a much better sense of where I stood.

“Hey, you should spank me, if you want to.”

“You should…” is definitely bolder than “Do you want to…?” or “I kind of want you to…” but I felt okay being bold in this case, because the person in question had already told me he enjoys spanking people. And we had been flirting a bit, so I ventured to guess he’d be open to spanking me.

Knowing this was a ballsy way to phrase my request, I opted to soften it by adding, “If you want to.” This builds consent into the statement. I probably wouldn’t use this approach with someone shy and accommodating, because I’d want to make sure they actually wanted to do it, rather than just agreeing out of a sense of obligation. But the person in this case was someone I believed would state his objections if he had any. Lucky for me, he was on-board.

“I wanna kiss you, but I’m nervous.”

I said this to someone who made me feel even shyer and awkward-er than I am normally. So much so, in fact, that my eyes were squeezed shut when I said this to him. Admitting my desire felt monumental, embarrassing, huge, even though I knew he wanted to kiss me too.

I often find that owning up to my anxiety – speaking it out loud – helps diffuse some of its power. Built into my confession is an unspoken request for validation. An understanding partner would respond with something like, “Aw, don’t be nervous. C’mere.” I think the person in question did indeed say something like that to me. But I can’t really remember; the excellent kisses have blurred my recollections.

“Would you like some boobs in your face?”

I said this to a friend while cuddling with her and another person in bed, and it ended up leading to my first threesome. She had mentioned that cuddling made her slightly uncomfortable because it’s so intimate, and that adding a sexual element can help mitigate that for her. So I offered up a solution that might make her feel better. All three of us knew we were headed toward threesome-town; this was my gentle way of setting that process into motion.

A lot of folks bristle at the thought of direct consent-asks – “Would you like…?” “May I…?” “Do you want me to…?” It’s true that these can sometimes be a bit clunky or unnatural, but I’ve never found that asking for consent “kills the moment,” no matter how artlessly it’s done. I’d always rather be too sure of my partner’s “yes” than not sure enough. Don’t let anyone shame you out of directness; it’s a good, useful, conscientious approach.

“I really liked going down on you and would love to do it again sometime.”

I sent this via Twitter DM, buried in a paragraph of spluttering explanations and excuses, because I was embarrassed by the intensity of my hunger for dat dick. This initiation probably would’ve been more effective if I’d just said it straight-up, instead of insulating it with clauses like “Sorry if this is crass and un-chill, but…” and “Feel free to ignore this if you think I’m being weird.” I already knew this guy liked having my mouth on his junk, so I didn’t need to be so cagey about what I wanted.

Enthusiasm is such a key part of an effective sexual initiation. In fact, I’d say that the basic recipe is “express enthusiasm + ask for consent.” Initiating sex isn’t just about asking, “Do you want to do this?” – it’s also about establishing, “…because I really, really do.”

 

What are your favorite ways to verbally initiate sex? What are the best initiations other people have said to you?