Dating Absurdities – The Juggling Act and Is It Ever Too Much?

Written by Sarah. Sarah is a first-time Jewrotica writer.

After ending a long-term relationship, I decided to jump back into the dating scene full force. I’ve never been one for scenes of any sort, but – given my tendency toward serial monogamy – I figured it was best to take advantage of this open window to indulge in the company of a handful of different men. Dating around can be time-consuming, however, those who are looking for more of a hookup than dating will use websites like Hookupsites.io, for example, to find someone that matches their criteria, it gets us to indulge in what we want, but for me, I wanted to indulge in dating.

And indulge, I do! My typical day looks like this: Work in the morning, take lunch outside, work in the afternoon, attend rehearsal for my dance company at night… and then squeeze in a date before heading to bed. Sometimes it feels a bit excessive (I went on five “dates” in the past four days with five different men), and I totally don’t want to keep up this pace (it’s hard to keep everyone’s family members and life stories straight!), but generally it’s been lovely.

They are all quality folks who know that I am not looking for a steady relationship and I do my best – in addition to enjoying myself – to be the best date they’ve ever had by focusing all my attention on them, being totally present, smiling and – as the 1950s as this sounds – making myself as beautiful as possible for them for the evening. However, this is not just it! The most effort I have ever put in for somebody would be when I arranged for a movie night for a person who I actually admired. Oh, the extravagances–flowers, lights, food, and whatnot! I even arranged for a big screen so that we can watch Netflix together. And not only that! Since the person I was dating liked classics, I happened to have used the fastest vpn for streaming the movies he wanted to watch (VPNs can help access movies that are blocked in specific locations).

So, as readers can understand, I do put a lot of effort. But now, I think that I need to put in less effort with people in whom I am not continually interested so as to send clearer messages, but my dates always leave me feeling kind of high on life and with boosted confidence (and we’re talking about a PG evening here!), so that’s good.

Anyway… last weekend, I attend a Shabbat dinner and meet this cute guy named Jake who coordinates a Jewish learning program on the Upper West Side. We hit it off, and a handful of us walked over to a local apartment to meet up with friends at the oneg (which is kind of like a Shabbat dinner after-party). Jake and I chat a bit more, he lends me one of his Jewish books for reading and – without missing a beat – sends me an e-mail the next day saying how nice it was to meet me, how he’d love to see me again soon and all this complimentary stuff.

I’m not such a quick e-mail responder and try to stay off the computer on Shabbat, so I don’t write back right away. But then Jake texts me on Sunday morning to see if I’m free and would like to go out together that evening. It seems like he’s super in to me if he’s sending an e-mail and a text the very next day, so I write back and we spend the afternoon exchanging texts. I decide to re-arrange my schedule to see him late Sunday night (after my Sunday afternoon date, which was a tennis lesson). I get all dolled up, go out front to meet him, open the car door and… it’s not him!!!

I repeat: TOTALLY not my guy.

But I know the dude and I remember that I’ve hung out with him at Jewish communal events before and then it hits me… Jake. This guy is also Jake, and he too grabbed my number at the Shabbat oneg to get together sometime.

I spend the next half hour laughing at myself because I totally did not intend on giving Jake #2 the time of day, but by virtue of his name, he “got lucky” and snagged an evening out with me! (His text had said “Hey Sarah! It’s Jake. It was so great hanging out last night, etc.” so of course I thought it was the first one.)

Anyway, it was clearly meant to be because – in addition to having a funny story – this Jake #2 ends up being really interesting and we have an awesome evening exploring parts of the city where I had never been.

I don’t know what my “lesson learned” is. Maybe that I should be more open-minded about giving people a first chance? Maybe that I should be dating fewer guys? But, until one snags me for that destined monogamous relationship, I’m going to keep on enjoying the hours of 9PM to midnight and keeping my eyes open for new lessons learned.