Pretty, Polite, & Pumped As Hell: How to Rock a First Date

I wore this in 2011 on my first date with the man who would become my first serious boyfriend. Aw, baby Kate.
I wore this in 2011 on my first date with the man who would become my first serious boyfriend. Aw, baby Kate.

Oh, first dates. Is there any situation more nervewracking, or more filled with potential?!

I get freaked out every time I go on a first date, even if it’s with someone I’m not especially excited about. I’ve been known to send panicked last-minute texts to friends while putting my outfit together: “What if he thinks I’m ugly or boring?!” “What if he’s a serial killer?!” “What if he wants to do [x sex act] and I’m bad at it?!”

However, once the jitters are sorted out and I’m on my way, I usually have a pretty good time. Whether a first date ends in passionate sex or a chaste cheek-kiss, whether it leads to something more or nothing whatsoever, it’s still an interesting opportunity to get out of your comfort zone and go on an adventure of sorts.

Here are my guiding principles for a successful first date. Of course, you could follow these to a T and still have a disastrously bad time… but at least if you do, it’ll be the other person’s fault and not yours!

1. Be on time. Lateness is the height of rudeness. A first date is like a sexy job interview: your aim should be to put your best foot forward and project the absolute best possible image of yourself. That means being polite and respectful, including in the way you manage your time. It’s good manners to be 5 to 10 minutes early for any appointment, but especially one as emotionally precarious as a first date. If you find yourself running late for any reason, notify your date ASAP, apologize, and keep them updated on your ETA. I know you’re not a jerk, so don’t act like one!

2. Dress well. Back in March, I wore a shirt with a hole in it on a first date. I’m not saying that’s why the relationship ended in bitterness and confusion, but I’m not not saying that, either. Look, I just think it’s a good omen to put effort into your appearance for a first date, both because it helps impress the other person and also because the spiffier you feel, the suaver you’ll behave. Your outfit should be setting-appropriate (probably don’t wear a church dress to a punk show, or a crop top to the symphony) and should make you feel badass and foxy. Bonus points if it includes at least one “conversation piece” (I like to wear my vulva ring on first dates, because, well, if someone’s not cool with that, there probably won’t be a second date).

What I wore on my "date" with Kidder.
What I wore on my “date” with Kidder.

3. Know what you want and be honest about it. Granted, not all first-date conversations meander to heavy topics like “What are you looking for?” or “Why did you decide to go on this date?” but if yours does, you should be prepared for that convo. If you’re only out for some casual fun, don’t tell your date you’re looking for something meaningful to pacify them; likewise, if you have your heart set on (eventual) commitment, don’t act like the Captain of Chill. It can be terrifying to frankly state what you want, but hey, dating is always a gamble. You’re far likelier to get what you crave if you’re able to ask for it. (And by the way: if you don’t know what you want at the moment, it’s okay to be honest about that, too.)

4. Have a solid pre-date ritual. This is crucial for me, as a person with anxiety. I need a Pavlovian get-pumped-up pre-date routine to banish anxiety and summon my best self. Mine involves loud, peppy music, lots of time spent on my makeup and hair, and texting with supportive friends. Get your prep on point and the rest of the evening will feel smoother for it.

5. Limit your substance intake. If you regularly partake of alcohol or drugs, I recommend you cool it on first dates. Even if your date matches you drink-for-drink, it probably won’t lead to good places: carrying on sharp conversations is harder when you’re blitzed, you don’t retain information as well, and you act different from how you normally would. If things get sexy, intoxicated consent is a fraught issue, especially with a new partner whose body and tastes you don’t know. Plus, if your date is someone from the internet or who you just don’t know very well, it’s safest to keep your wits about you, just incase. I know those soul-searching, three-beers-in conversations can be great fun – mulling over life’s big questions together while getting progressively flirtier – but maybe save those until you know this person a bit better, mmkay?

6. Pick a place where you can talk. In my experience, lots of folks get nervous about not seeming “cool” or “fun” enough to a new potential partner, so they’ll try to take you to some Mega-Awesome Thing like a stand-up comedy show or a drive-in movie theatre. It’s my staunch opinion that all first dates should be “let’s talk and get to know each other” dates. It’s best if this is a low-commitment situation like coffee or a drink – as opposed to a full meal, where you’re stuck in your seat for at least an hour even if the two of you end up hating each other. All my best first dates have involved going out for some kind of beverage together and talking for hours. If your conversation crackles and flows, that’s hugely useful information that you totally wouldn’t have found out if you’d met at a loud punk bar or arthouse cinema.

What I wore on a Tinder date in Minneapolis.
What I wore on a Tinder date in Minneapolis.

7. Be prepared for sex. Responsible adults know that dates might lead to sex and sex carries risks. If you’re going on dates without safer-sex supplies in your bag/pockets/car, what are you even doing?! In addition to condoms and whatnot, you should also prep your body and mind in whatever ways make you feel sex-ready – you don’t want to be in bed with your gorgeous new lover later tonight and find yourself unable to focus on anything but your prickly legs and musky junk.

8. …but don’t feel obligated to get sexy. There are all kinds of “rules” about sex on first dates. Some say it ruins a budding relationship; some say a sexless first date is a disastrous omen. The truth is, there are no set-in-stone timelines for how dates or relationships are “supposed” to go. If both people want to have sex and are emotionally and physically prepared to do so, there’s no reason why they shouldn’t – but there’s no rush, either. You do what feels right for you and don’t let anyone shame you. If your date is The Right Person, they’ll be on the same page as you about sex stuff – or they’ll be willing to get on the same page as you.

9. Ask them about them. My number-one complaint about most boys on Tinder is that they’re terrible conversationalists. Don’t be that guy. Be interested in your date, ask questions and then follow-up questions, and really listen to what they say. Strangers often seem boring until you discover what’s interesting about them. Give them the opportunity to show you that, by asking them about themselves. (This has the added effect of making you appear to be extremely charming and socially skilled. Yay!)

10. If it sucks, leave. Like Alana Massey says: “Stop wasting your time on bad first dates.” If someone is rude, or boring, or wants different things than you do, or you just don’t find them as attractive as you thought you would, you are not obligated to continue with the date. Be polite and respectful (if you can) when you duck out, but don’t let yourself be guilted into prolonging an encounter that’s absolutely not working for you. Those of us raised female (or Canadian) are especially prone to feigning enthusiasm for the sake of politeness, but you don’t have to do that. You deserve better than that.

What are your first-date commandments? What are some of the best and worst first dates you’ve been on?

“Sex Blogger” Is Not My Entire Personality (+ How to Date/Court a Sex Blogger)

Here is a paradox for you:

When I do any kind of online dating, or even (gasp!) in-person dating, “I have a sex blog” is one of the first pieces of information I always reveal about myself. It acts simultaneously as a conversation starter and a filter, scaring away the people who are intimidated by open sex-positivity while pulling in those who are intrigued by it.

But it also starts the interaction on a wacky, imbalanced note – because everyone has different notions about how they “should” talk to a sex blogger, and it’s rare that that notion is just “treat her like a regular person.”

 

I recently made the not-entirely-thought-out decision to link my Tinder account to my Instagram page. Naturally, a sea of dudes immediately followed me. The number of messages in my Tinder inbox, and the intensity of their creepiness, shot up.

This shouldn’t be surprising. And some people would say, “What did you expect? Why do you put that information in your profile if you don’t like the reactions it gets you?”

This feels like borderline victim-blaming, but I’m not even 100% comfortable making that claim. Because, yes, I am a sex blogger and should therefore theoretically be okay with receiving sexual attention. It’s what I’ve “signed up for,” especially when I’m interacting on already-sexual platforms like Tinder.

But, ugh. I don’t mind if people get sexual with me sometimes – it just has to be consensual, and for fuck’s sake, polite.

 

I think it surprises some people to discover that although I am a sex blogger, I am not actually a nymphomaniac. (There’s nothing wrong with having a super high libido or with pursuing lots of sexual experiences and/or partners. That’s just not really who I am or what I do.)

I have always had an interest in sexuality as a topic. It’s almost a theoretical or academic fascination for me. I know a lot about it, I think a lot about it, I find it compelling to talk about and learn about – but my life doesn’t actually revolve around the act of sex itself. I, like most people, am way more complex and nuanced than That One Thing you happen to know about me.

When someone learns about my sex blogging right off the bat, too often they put me on a weird pedestal where I’m supposed to perform the role of the “sexy lady.” I feel boxed into explicit conversations, high expectations, and being “up for anything.”

And let’s be real: I am definitely not sexy 100% of the time. I am goofy and strange, shy and awkward. I have interests and hobbies (so many!) that have nothing to do with sex. And if I’m going to date someone – or even just fuck them – I want them to know that. I want them to see the totality of me, acknowledge me, accept me, approve of me.

 

I’ve been dating a lot lately (ugh!/yay!) and have encountered two dudes who illustrated polar opposite ends of the “how (not) to treat a sex blogger” spectrum:

One guy fixated on my sex-related work. He asked me endless questions about my personal sexual tastes, which is pretty inappropriate for someone you’ve just met. He took my work as an invitation to fast-track our relationship toward sexytimes, even as I was pretty clearly pumping the brakes.

I tried to introduce other aspects of my personality, and other hobbies of mine, like I would do with anyone I was getting to know. I mentioned my journalistic work, my music, my improv background. I also asked him about his work and hobbies, scrounging for anything to talk about other than sex. But he kind of ignored me and kept hounding me about my sex life, fantasies and desires, as if there was literally nothing else of value in my whole brain.

The second guy, thank goodness, treated me like an actual human. We talked about my work, and he clearly found it interesting, but he didn’t press me for details and we didn’t get too personal. He’d periodically make a comment like, “We can talk about something else if you want; you probably get tired of talking about this stuff,” giving me an opportunity to change the subject if I wanted to. But because he was being so respectful, I actually loved our sex chats. He understood my fascinations with things like sexual ethics and the origins of kinks, and we talked for literal hours about sexuality in a way that was neither boring nor creepy. We also talked about other interests and pursuits, mine and his.

This guy was hesitant to make a move – not that it’s always the man’s responsibility to take initiative, because it isn’t – and it turned out he was worried I’d think he was creepy if he assumed I’d be DTF just ’cause I’m a sex blogger. I was DTF, but it wasn’t because I write about sex – it was because I loved spending time with him, felt totally comfortable with him, and found him incredibly attractive. (Amazing how sex bloggers’ attractions work just like other people’s attractions, huh?!)

 

This has all been pretty rambly so far, so here are some actionable items if you want to interact with someone who blogs about sex or works in some other sex-related field. (Keep in mind that these suggestions are based on what I prefer and value; as always, everyone is different so your mileage may vary.)

  • Ask me about non-sex-related stuff too. Remember that sex blogging is my job, not my whole life. Would you ask your dentist friend to look at your teeth on the daily? Would you ask your lawyer friend to explain tort law to you when they’d just worked an 8-hour court day? Probably not. I have other shit going on, which I will gladly tell you about if you ask me what’s up. Listen, pay attention, follow the natural flow of the conversation like you would with any normal human.
  • Give me an “out.” Despite what I just said, I actually do like talking about sex – in the right context, with the right kind of people, some of the time. I work in this field because it fascinates me. If you’re getting the sense that I might be uncomfortable or bored with our current conversation, give me an easy opportunity to shift topics. I will if I want to.
  • Don’t get too personal. Unless we’re close friends, fucking on the regular, or maybe slightly drunk, I probably don’t want to tell you about my kinks and fantasies in too much detail. They might come up in the course of a conversation but please don’t badger me for specifics and examples. If I feel comfortable with you and it feels appropriate for the type of conversation we’re having, I might open up, but I’m not required to.
  • Likewise, don’t dump your TMI sex secrets on me. Or at least, don’t assume it’s okay to do this. There are definitely contexts in which this is okay and feels natural… but please oh please read my non-verbal and verbal cues and stop that shit if I seem uncomfortable. (Or just ask, “Is this okay? Do you want me to stop talking about this?”) I may not feel able to straight-up tell you, “I’m not comfortable talking about this,” either because I don’t know you well enough to know if I can trust you or because I am trying to be sex-positive and avoid shaming you for the desires or experiences you’re expressing to me.
  • When bringing up stuff you’ve read on my blog, my social media, etc., start small and see how it goes. It is gross if you immediately say something like, “That selfie you posted today gave me a boner,” or, “Reading your review of that dildo made me wish I could use it on you.” (You would be surprised how many guys think it is okay to open with lines like this!) If you want to talk about something you saw me post online, bring it up subtly, tactfully, and in such a way that I can easily navigate away from the topic if I’m uncomfortable.
  • Don’t assume I want to fuck you. It is okay to flirt with me, respectfully; it is okay to have a crush on me, and to express those feelings; but please don’t take my sex-blogger-ness as a substitute for the positive signals you would normally look for when flirting with someone. If I’m talking about sex a lot, it may or may not be an indicator of my feelings for you – but if I’m laughing at all your jokes, blushing, giggling, maintaining eye contact, leaning in close, making excuses to touch you, and doing all the other things that smitten-and-flirty people do, then you can take that as a green light, same as you would with any kind of person. ‘Cause guess what? I am a person!

 

Sex bloggers and other inhabitants of sexual fields: how do you navigate the dating world while being true to yourself but also discouraging creeps? Non-sex-world folks: is there anything else you’d like to know about how to approach dating/courting/fucking people like me, in a respectful way?

How to Date When You Have Anxiety

“You should write a blog post about how to date when you’re an anxious person!” my friend said excitedly, as we gossiped about boys (and mental health struggles) over lattes and cupcakes.

“HAAHAHAHAHAhahahaha,” I replied. “I have no idea how to deal with my anxiety while dating. I barely even manage it myself. How can I tell other people how to do it?”

The more that I thought about this exchange, though, the more I wondered if I could actually be more helpful than I’d realized. I don’t think you have to be an expert in order to help someone. The experiences you’ve had, and the lessons you’ve learned, can be of use to others even if you’re still in the midst of your own journey.

So, with that in mind, here are some things I’ve learned about navigating the dating world when your brain’s fear-meter is a little out of whack. I hope this helps you, at least a little.

1. Enlist socially competent friends.

It feels a little “high school” to constantly text friends whenever anything happens with your crush, I know. But if you’re lucky enough, as I am, to have friends who appreciate (or at least tolerate) this behavior instead of blocking your number, I think you should let those friends support you and help you.

Here are some examples of ways my more socially skilled friends have saved my ass when anxiety was clouding my brain:

• I texted my pal E., “[Boy] said he might want to see a movie with me today, but now I feel like it would be too forward for me to text him and ask him about it!” E. reminded me, “[Boy] said he wanted to see a movie with you, so it’s not forward,” and then suggested a possible wording for the text I could send. What an angel.

• I spoke to a number of friends about the situation with a boy I liked, and several of them said, “Go for it!” I wasn’t really sure what this meant, precisely. I asked my friend E. what he meant when he said “Go for it” and he said, “Tell him you like him, or ask him out.” Ahhh, okay, I thought. The specificity helped.

• While chatting with my friend A., I listed a bunch of things that [Boy] had said and done the last time we hung out, all of which I thought were ambiguous and could have been flirty or just friendly; I really didn’t know. When I finished, A. laughed for a good minute and said, very sarcastically, “Yeah, he’s totally just into you as a friend.” Her third-party viewpoint helped me see what my anxiety had been hiding from me.

• Soon before my last break-up, I realized I didn’t actually know how to break up with someone. People kept telling me, “Just get it over with!” and “Be respectful but firm!” but I was missing basic information like where to do it and what to actually say. My pal A. helped me rehearse a little script and weighed the pros and cons of various break-up locations with me. We even discussed what to wear to a break-up, because that’s the kind of thing I worry about.

See? Friends can be sooooo helpful when your brain is being your worst enemy.

2. Journal about it.

Where would I be without journaling? Maybe dead. Definitely sad and confused.

I find journaling absolutely essential as an anxious person because it helps me process all my zillions of thoughts. I can go on a 5-page-long ramble about all the worries and insecurities I have around a particular situation, and by the end of it, a) those thoughts no longer occupy my brain quite so firmly, and b) I can see very clearly just how ridiculous those thoughts are. Journaling gives me some distance, some objectivity.

I can also tell you from firsthand experience that it is hilarious to re-read your old journal entries from the nervous beginnings of relationships. “You silly twit,” you’ll shout at your past self, “of COURSE he meant he liked you when he said ‘I like you’!!”

3. It’s okay to be honest.

Sometimes when I start dating someone, or even when dating seems possibly imminent, I’ll bust out a little speech. It goes something like this:

“Hey, so, just so you know, I have anxiety. That means that sometimes I’ll get really nervous around you and act weird. It doesn’t mean I feel uncomfortable or unsafe with you; it’s just how my brain works. I also might need a little extra reassurance and validation from you sometimes, because my anxiety is always telling me that people don’t like me and that I’m worthless. So if you could try to assure me once in a while that you actually do like me, that would be really helpful. I’ll try not to be too weird.”

People tend to respond favorably to this kind of honesty, actually. Some people even find it adorable. (That’s a whole other can of worms – my mental health issue is not cute, okay?! – but it’s certainly better than them shaming me for my anxiety or dumping me because of it.)

4. Find your self-care practices and use them.

Here are some things I like to do when I’m getting ready to go on a date or to spend time with someone I like:

• Spend ages choosing the ideal outfit, doing my makeup and hair, and making sure I look adorable. (Some would call this obsessive, maybe, but it helps me calm down.)

• Make sure I know, with 100% certainty, where we are going, how much it’s going to cost, what time I have to leave my house in order to get there on time, and any other relevant information. (I eliminate all possible stressors. This is an act of self-love and self-protection.)

• Play Scrabble on my phone while traveling to the destination. (It calms my brain somewhat, by giving me something to focus on besides my stomach-curdling fear. Podcasts and music also help.)

• Breathe deeply and slowly. (“Fear is just excitement without breath,” after all.)

Whatever your own self-care and self-calming practices are, make sure you actually remember to do them when you need to. It might be helpful to write them on a card and keep them in your wallet, or set them as your phone background, or whatever. Keep ’em close and do ’em often.

5. Assess the situation objectively.

As objectively as you can, anyway. I know it’s difficult.

If you find yourself thinking an anxious thought – for example, “He doesn’t like me anymore!” – look for evidence of that thought. Odds are, there won’t be as much as you thought (or any).

Then look for evidence of the opposite thought (e.g. “He likes me a lot!”). There will probably be some.

Breathe. It’s okay. Your fear is inside your own head and nowhere else. You don’t have to listen to it. It doesn’t reflect reality.

Anxious folks: how do YOU navigate the dating world without vomiting on your suitors’ shoes?

Sharing the Sexy #30

• Everything you ever wanted to know about foot fetishes.

Dating tips for feminist men. There needs to be more resources like this!

• Here is a zine on learning good consent.

• This is also a really great consent resource, including sample scripts for consent-related conversations you might have with your partner(s).

Why does spanking feel so good? (When I saw this, it made me wonder if Lelo is thinking of releasing a paddle… Think it could rival this one?)

• The Red Tent Sisters weigh in on how to ease into using menstrual cups for the first time.

• Lilly drops some truth bombs about sex toys and body size.