So it’s been four long years since the last Biz & Blerg Blove Blog. Seriously. While things may have changed for Blerg, things have definitely not changed for Biz. So, a few days after my 35th birthday, I decided that it was time to do to dating what I’ve already done to my dry cleaning, grocery buying, driving, and a half-dozen other mundane tasks I can throw money at to make happen for me. That’s right: I signed up for a matchmaking service.
To preface why I decided to go down this path, it’s actually pretty straightforward. I haven’t been in a relationship, seriously or otherwise, since I was 18. I’ve gotten close once or twice, but it never happened. To put it another way, the last time I was in a Facebook Official relationship, Facebook didn’t exist yet. As has been endlessly documented elsewhere, I’m pretty much an Unmatchable on literally every online dating site in existence and unless someone is literally holding a sign that says “Please ask me out, Biz!” right in front of me I probably won’t have the where-with-all to ask them out. Moreover, once you cross the Maginot line of dating in your late 30s, it gets exponentially worse, much as it got worse once I hit 30.
This is pretty much what matchmaking exists for – to drag reclusive shut-ins with at least some redeeming qualities (oh hey, that’s me!) out of their lairs, into the sunlight, and get them to interact with members of the preferred gender.
Before I started this particular journey, I had assumed that matchmaking was the kind of thing that, even with the means at my disposal, was beyond my ability to take advantage of. Well, I was sort of wrong. I’m not going to say the package I bought is cheap – it’s roughly the equivalent of three and a half years of premium membership to an online dating site – but it does potentially offer a much higher return on investment. Instead of going on a hundred shitty dates, I’m going on three really good ones, which will be curated experiences provided by the company that will be something we’ll both enjoy.
Or, at least that’s what was promised as part of the sales pitch. Reality has a funny way of making a mockery of marketing materials.
So, with that being said, let’s start with the onboarding process.
I reached out to the company I picked for this endeavour at the suggestion of a female friend who is in similar straits to myself – unlucky in love, living in a major city, and generally looking for something to break up a seemingly endless streak of bad luck. They contacted me within a day or two and scheduled a brief phone interview. The phone interview, near as I can tell, was to make sure I wasn’t completely undateable. It was, admittedly, an occasionally awkward conversation – explaining what I looked for physically without coming across as misogynistic or creepy was admittedly challenging, but based on the results I think I got my point across well enough.
After a background check, I got introduced to my matchmaker. Depending on the package, you could either pick your matchmaker or be randomly assigned one – I decided to roll the dice and went with randomly assigned. We did a video introduction via WhatsApp, and she got on looking for prospective dates for me.
The package I selected came with three dates over a three month period – I was guaranteed three dates, regardless of time, but the goal was to get them done within three months.
After a few weeks of silence, my matchmaker set me up with my first date in early April. She sent my date and I to a Russian restaurant in the Loop here in Chicago, which didn’t exactly scream “romance”. However, the date itself was good. My date and I had a lot in common, moreso than I usually have, and we agreed to meet again, this time somewhere less eastern European. She had expressed a fondness for Ethiopian food, so I picked dinner at an Ethiopian restaurant equidistant from our neighborhoods. We went, had a good time, and promised to meet up again. I texted her a few days later to set something up, and she said that she wasn’t interested.
After that. my matchmaker set me up with another woman a few weeks later around mid-May. This time, my matchmaker had me venturing out to the suburbs. I explained to her that I wasn’t really looking to travel 45 minutes each way to go on a single date, much less establish a relationship where that was a requirement, and that I doubted my date would either. My matchmaker made me a deal – if the date went badly, she’d comp it. Fair enough – worst case scenario, I get a free date.
Well, I traveled out to the suburbs and got to the restaurant a little early. My date was 20 minutes late due to traffic, then the restaurant sat her at a totally different table, so the two of us were texting my matchmaker trying to figure out what was going on. After getting that sorted out, we sat down and started to chat. After about fifteen minutes, it was obvious that this wasn’t going anywhere. We had very different interests, goals, and life paths mapped out, and basically ran out of stuff to talk about before our entrees arrived. I went back to my matchmaker after the date and explained that that was a sub-online dating quality date – I would have screened her out based on distance alone, not to mention the total lack of anything in common. My matchmaker was suitably chastened, and comp’d the date.
Next, she set me up with another woman, but I had to wait three weeks before she was available. I’m patient, so I said fine. My matchmaker was really excited about her, so I figured hey, why not. Well, as the date came closer my work travel schedule unexpectedly interfered so I had to reschedule. My prospective date wasn’t available for another six weeks after the original date, so my matchmaker cancelled the date.
As for my actual second date, that happened a few weeks later. We met at a little Italian place in Wicker Park, got some appetizers, and took a walk on our way to get some Italian ices. It was pretty unremarkable – there just wasn’t a spark there. We parted at the end of the evening with a promise to get together for a second date in a few weeks, but it never happened.
At this point, I was feeling pretty ambivalent about the whole process. I had been on three dates – one was really good but went nowhere, the second was bad, and the third was so-so.
That brings me to my third date.
My matchmaker promised me that this would be the best date yet – that she had found someone that was perfect for me and was sure we’d hit it off. I was skeptical, but enthusiastic. Well, she delivered. My third date was with a woman who worked in tech (check!), lives down the street from me (check!), is the Star Wars trivia champion of Chicago AND has her own Star Wars podcast AND likes to go to conventions (check!), and was very attractive (check!). Basically, everything I was looking for. We started talking, and really hit it off. We blew through two hours, two glasses of wine each, and a charceuterie board before we had to part ways. It was torture waiting a few days to let her know I wanted to see her again. The feeling was mutual, so we agreed to meet up about two weeks later.
We exchanged a few texts over the weeks, then I asked when she wanted to meet again. Silence.
I waited a few days to text again and see when she wanted to meet. More silence.
Yup, I got ghosted.
At this point, my matchmaker had fulfilled the contract, so now I started getting emails and notes about signing up for more dates. At first I demurred because I was really hoping Date #3 would go somewhere, but when it became clear that that wasn’t going to be the case, I basically just shut down. There comes a point where you accept that what you’re offering to the world as a partner in a relationship just isn’t enough, so rather than keep spinning my wheels and hoping that things change, I figure at this point it’s better to just live my own best life, and if someone comes along that wants to share it, so be it.
