In Which I Attempt to Give Tips on Dating

There is all sorts of advice out there about meeting people and dating them. Most of them are far too scripted and full of assumptions to be all that useful in real life. Allow me to contribute a few to the list that have sometimes helped me. In no particular order:

My Five Dating Tips

Tip #1 If you’re new to dating, don’t get discouraged by failures, BECAUSE JUGGLING!

I first started trying to date in high school, and for quite a while I experienced literally nothing but rejections. I spent a lot of time being angsty and I was pretty well convinced the book was closed on my ability to ever date (seriously, in old Livejournal entries, I “give up on finding love” practically every other week). If I could talk to myself then, I’d say roughly this:

Try juggling 10 times in a row. If you’ve never tried before, you’ll fail every time. If you assume that means you’ll never get the hang of it, though, you’re being silly. Your first tries aren’t representative of your potential. Hell, I couldn’t juggle at all the first 100 times I tried. Probably took 500 or 1000 or so before I could consistently keep 3 objects up in the air. If I had assumed my ability would never change based on my first few attempts, well, I would’ve been thinking about it all wrong. You get better at all this shit with time.

When you’re starting out, you’re still getting the hang of everything, including talking to people you’re interested in. You may have been rejected a whole bunch of times, feel “incurably” nervous around people you’re interested in, whatever. You’ve got your entire life to practice and figure this stuff out, and there’s absolutely no point or accuracy in judging yourself based on your first few years unless you let it become a self-fulfilling prophecy by giving up. Thing is, that’s the same as giving up on being able to juggle because you can’t do it the first 10 times you try. Of course you can’t. Because it’s the first few fucking times you’ve tried! Sex is complicated, people are complicated. When it comes right down to it, moreso than juggling.

Most people suck at this shit starting out. That’s because it takes a while to figure it out. I’m still figuring it out, but now I know what I know: the things I still haven’t got the hang of, I just need a lot of time and a lot of practice to get them right.

Tip #2: Wear conversation starters. For best results, wear targeted conversation starters.

I do this halfway intentionally and halfway accidentally. You can tell I’m a geek from a long way away. From closer, without too much trouble, you can tell that I’m poly and kinky as well. Most of my wardrobe is geeky in some form or another. I have jewelry and even belt buckles with geek/kink/poly bits on them.

What’s the hardest part of approaching someone you want to talk to? For me, at least, it’s having a thing to say. If someone’s wearing, say, double-helix earrings, though, then I both (a) know there’s a much better-than-averge chance we’ll get along, and (b) have something to start a conversation with. Correspondingly, I know it’ll be easier for people to approach me if I wear things that start conversations, and it’ll be more likely they’ll be conversations I want if the things I wear communicate what type of person I am. Last month at a con, for example, some kinksters completely unknown to me introduced themselves after recognizing a kink-themed shirt of mine.

This is a big help for meeting people in general, as well, not just dating.

Tip #3 A simple trick for maintaining tension through establishing consent

So, consent is important, but it’s easy to worry that it will ruin the moment. Generally, I find that moments are far more often ruined by crazed obsessing over the maintenance of the moment, so before I continue let me say that I think the ideal is to just stop worrying about it in the first place. Think of this tip as training wheels to move you toward the goal of just not giving a shit about moment-ruining. I haven’t done it much recently, but it has a fond place in my heart from earlier dating escapades. Bear in mind that like all things that follow any sort of script, context matters. This isn’t appropriate for all situations. If it fits the situation, the person, and the vibe, though, it’s highly enjoyable. At least, I’ve found it so.

The trick is: if you want to, say, kiss someone, ask for consent. Then, if they consent, and you feel the lovely tension is somehow broken, tell them you will kiss them. Soon (generally for me this has been within a couple of minutes of “soon”).

You want a good tension builder? Make it so someone knows a kiss that they want is coming, but they don’t know when!

Tip #4 Make the giving of compliments its own reward

It’s good advice for all of life, but in particular it’s helped me learn to communicate my attraction to people in noncreepy ways.

A few years ago, one of my friends told me they were attracted to me. I didn’t reciprocate, but it was still an awesome thing to hear. I think about things like that years later and they still make me feel good. The feeling that comes from knowing that someone you respect finds you attractive is awesome.

At some point over the last year or two, I realized that giving people that feeling is its own reward, and suddenly I was a lot more comfortable telling people I was attracted to them. I was more comfortable with it because knowing I might be making someone feel good that way made the compliment its own reward. Making the compliment its own reward meant that it didn’t matter so much if the person reciprocated the attraction or not. Obviously I still like it when attraction is reciprocated, but these days I find it much easier to be pleased with having told someone I’m into them even when they don’t reciprocate. I know, if they respect me as a person, that they’ll probably really appreciate that I’m attracted, even if they don’t reciprocate.

This means I can tell people I’m into them much more comfortably, without those people feeling the weight of expectation and how-do-I-tell-them-I-don’t-reciprocate that often accompanies the expression of interest. The fact that I’m enjoying the compliment for it’s own sake tends to show through in the delivery.

If I’m worried it won’t show through, in particular if it happens to be an online conversation, I’ll occasionally add something like the following:

“Disclaimer: I’ve always really appreciated when people have told me this kind of thing; I’m not telling you it to ask for reciprocation; just because I like hearing it when it’s directed at me, and I assume other people like hearing it, too, so I try and share when I can.”

As always, Franklin Veaux writes very well about this idea also.

I’ve gotten much more comfortable expressing attraction to people since I’ve started thinking about it this way, and as a result, I’ve discovered that a lot of the people I’m attracted to are attracted back, but were just as afraid to express it as I was.

Tip #5 Think less about what you do, and more about how you feel

So much dating advice is about what to do. That isn’t, as a general rule, nearly as important as how you think and feel about dating. Keep that in mind. Emily Nagoski talks about this better than I could, so I’m going to yield the floor to her on this one.


There you have it: a few things I’ve picked up over the course of my dating career that I’ve held on to. Hope this helps somebody.


4 comments on “In Which I Attempt to Give Tips on Dating

  1. My wife and I are rapidly approaching ten years since our first date, married over 6.

    A week or two before we went out for the first time I went to an auto show with two of my friends from high school. We were driving, and I said, “There’s this girl that I met in school. She’s cute, but I don’t think I’d ever date her, she’s kinda weird.” She thought I was the weird one. One friend from that night was my best man, one was another groomsman.

    We were both in culinary school at the time. We started going out and never looked back. My best dating advice is never count out the people that you may dismiss out of hand. You never know! She was my first date in ~2 years.

    • Interesting. I actually would say I tend to rule people out after not a lot of interaction fairly often (at least, rule them out in the sense of thinking of them as potential serious relationship partners). I tend to have powerfully intuitive responses to people that seem to, generally, be accurate predictions of general compatibility. I could be putting too much stock in that, though.

  2. Thanks for this. I’ve been vaguely trying to get back into the swing of dating for a while now, and #4 is especially helpful advise. It’s something that I used to do well, probably because I wasn’t “trying” to do anything, but I suppose that just shows how out of practice I am.

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