So I went on a week of crazy dating. I wanted to learn some things, like, can I connect with random people? Can I have satisfying conversations even when there’s no chemistry? Here are the events, and their lessons.

week saying yes to dating

So I did a little experiment in the last week. I started saying yes on dating apps and websites to anyone that seemed remotely interesting or interested. I wanted to see what would happen if I agreed to meet lots of people. Am I being too choosy? What if I’m missing out on great potential connections?

So I made an already busy week much busier by meeting up with gents (wish I had gotten some ladies as well, but whatevs, that’ll happen eventually) and trying to see if I could get a few more connections/lovers/play partners in my life.

Dating Week, #1: Military Guy

It all started with Military Guy, with whom I’d been chatting for a couple of days on POF. There was no chance of us doing more than hang out, but I still invited him for hanging out on his last night in my town. He was smart and we had great conversations. We tried a new restaurant that had just opened a few days ago (delicious!), we walked a little around the waterfront, and then we went to the local board game café for milkshakes and some games (we played Kulami). Which was fun.

It was a great evening, all in all. I had fun, enjoyed a nice evening out, had some interesting discussions, and managed to spend a Saturday night doing something social. Even though there was nothing else to expect from this meeting, I’m glad I went.

Dating Week, #2: The Economist

The next one was with The Economist. I’d answered his intriguing ad on Fetlife earlier the week before, and we planned for a coffee date on Monday.

Although he’s a bit on the younger side than my usual dating interests (he’s younger than my brother!), his smarts and geekiness convinced me that we’d at least get along in a friendly way. Which is what happened. The hour sped by, and I had a really good time. We come from different sides of academia—him in economics (duh) and me in humanities, and it makes for really interesting conversations looking at problems from completely different directions. I love to learn new points of view and approaches, so that was fun.

As someone who’s been told she doesn’t look kinky (whatever the hell that means), I kind of am fascinated by the hidden sides of people and what they hide behind their masks. The Economist looks cute and inoffensive, and I’m really quite curious to see what his toppy, Dommy side looks like. We’re already planning a simple scene to start… locks and chains, yum!

Dating Week, #3: The Dog Lover

Then on Tuesday there was Dog Lover. We exchanged a few brief messages on POF and I agreed to meet him, not really knowing if we have much in common. Sometimes you just gotta give it a chance. I called him Dog Lover because one of his pictures has him cuddling with a dog.

Well, it turned out I should have stayed home. My feeling was correct, we didn’t have much in common and the date was, to say the least, boring. He kept looking away from me as if disgusted by my actual weight (which I don’t hide in my photos, at all) and even though I tried to keep him engaged in conversation, it was like pulling teeth. He was cute but not very interesting, without any passion that I could see. He ended the date with “Let’s say in touch,” and I was like, “No.”

Oh well, I’ll consider this training for my future as a therapist who will sometimes have to pull teeth, I guess.

After that, I went to a munch, arranged another date with someone from the community (or at least got his number) and then got beautifully and royally beaten and fucked by C. He calls me “Princess” for a reason!

Dating Week, #4: Sunglasses At Night

Another POF find, Sunglasses At Night was a nicer chat than Dog Lover, but still no chemistry. He asked me questions and got me talking (which I love), but in the end it was a no-go.

Sometimes I wonder if I should bother dating outside of the community at all. I mean, there are potentially kinky people out there who just need to be guided to the community (thinking of a friend whom I introduced and he now has a wonderful relationship with a woman in the community), but the drudgery of meeting them and figuring out whether they’re interested or going to slap me with some Bible drivel is not really productive.

(Not that this is what happened with Sunglasses At Night. He was a gentleman and listened and asked questions.)

So, I don’t know. I know there are wonderful vanilla people out there, but the question is, do I want to date them?

Dating Week Results: Meh

First, I’m really not meant to handle so much social in so little time. I’m now exhausted and just want to lie on my couch and cuddle my cat while watching Outlander.

Although I did have one successful date out of four (it’s not really a big sample, but bear with me), I’m not sure I’d do something like this. I really lowered my standards—by not chatting more extensively with potential dates and making sure we got along BEFORE accepting to meet them. That would have saved me the awkwardness of Dog Lover, and probably would have told me not to see Sunglasses At Night either.

In the end, although it was an interesting experiment, I think I need to be more choosy about who I meet. Meeting in the community is best, because at least I know people have similar interests and are committed to improving their kink lives, but I won’t say no to meeting someone I get along with who might be vanilla.

I also learned about the limits of my introversion—I really can’t go out talking to people every day. I’ve been out pretty much every day for over a week and I am exhausted, mostly emotionally. Even though not every outing was a date, I still need time to replenish and re-energize. So I need to be more careful about spreading out my social events and leaving myself enough time to recover.

So, all in all, it was an interesting week, but I wouldn’t do it again—with dates with C., and seeing E. more often lately, and possibly getting a new partner in The Economist, I doubt I’ll have much time for anymore dating. Also, I’m going back to school in September (yay!) so I will have even LESS time for seeing people.

Lessons, itemized

  • Be a little more choosy in who you accept to meet by talking a little more with them
  • Only meet those who you think you might have chemistry with
  • When in doubt, don’t bother
  • It’s okay to meet new friends, as long as it’s clear that it’s just friends
  • The community is a good place to start for more compatible lovers


Good advice? Helpful information? Thank me with a coffee!