The Spinster Chronicles: When first dates feel like job interviews

Are you Bumbling your way through apps and online dating? Do first dates feel just like job interviews? Our favourite spinster Jennifer Walters is back, candidly sharing her dating debacles with us.

First Dates: The Interview Process

‘I don’t like to talk to people on the phone. I barely like to talk to most people in person, but voice to voice with someone who I’ve only known as still images of him and his dog or posed candids of him scaling Mount Everest is extremely painful and accelerates my normal awkwardness toward a full blown display of embarrassment during which I forget simple English and fun facts such as how old I am.

In-person there would be, at least, wine and fake smiles to fill the inevitable conversation lulls. During a recent interview, I mean phone call, I found out that Dude is very enthusiastic about their career but also super excited about his new adventures in snow sports. He told me how much he works out and how he enjoys wine but only sociably because he doesn’t like to “overdo it or anything.” He ended the conversation abruptly because he got a call from his sister in the midst of me sharing with him how often I DON’T work out, how often I DO drink wine with ZERO dependency on whether or not I am in a social setting, and my complete lack of desire to ever do anything that involves snow.


He did not call me back. He did, however, send me a message on the dating app informing me our conversation was “dry” and we probably shouldn’t bother talking again. I can’t say I disagree but for some reason his acknowledgment of the obvious was quite the blow to what’s left of my already defeated ego. A mutual ghosting would have been much more polite. All part of the first dates interview process I guess.

11th February 2021

I was supposed to go on a date last night. He cancelled on me because something came up with his son, he had an appointment to show a house he forgot about, and he couldn’t figure out his password for the Higamahoo website, but hoped I’d give him another chance on another day.

I told him I understood things with kids, empathized with his inability to logon to and yes, I’d give him another chance, although he clearly might have time management issues if he booked a showing and date with me for the same time, same day.

I then realised I didn’t know his last name and should probably figure that out so I can search for a criminal record before we make plans again. I googled his phone number and found a last name that looked familiar, familiar as in New Guy has the same last name as Poop Doctor. (See previous Spinster Chronicles article)

I then googled New Guy and Poop Doctor together and found an old blog post from Poop Doctor talking about his life (which he thinks is amazing, if you don’t recall from when I told you about my date with Poop Doctor a few weeks ago), including how excited he was when his baby brother New Guy was born. I texted New Guy and asked if he had a brother that is a poop doctor. He does. I mean, come on, what are the chances?

13th April 2021

It was seven o’clock, on the dot, in my drop top – kidding – I just have that song stuck in my head, which is odd because I usually only get that song stuck in my head around midnight when I can’t sleep and should be counting sheep. Instead, I am fantasizing about meeting Usher in the Harris Teeter parking lot after hitting his expensive car with a shopping cart, our subsequent falling in love, being endlessly harassed by the paparazzi, and me eventually breaking his heart because I’m not cut out for a superstar lifestyle.

It was actually seven forty-five-ish and I was in the midsized SUV that I purchased after years and years of shaming from my sister-in-law for driving a “mum van”. I pulled up a bit nervous because MfromTinder had some questionable fashion choices in some of his profile pics. But as my friend and confidant Stacey says, “it’s a lot easier to get a man to give up a bad chef pants habit than a bad cocaine habit,” something with which we both, unfortunately, have way too much experience. So I proceeded with cautious confidence that he wouldn’t be dressed like a Culinary Arts student from my mid-1990s high school vocational training program.

MfromTinder texted me to let me know he was running late because he went to the wrong restaurant. Midway through my glass of wine, I decided I’d prefer if he didn’t show up at all because I was really enjoying my book, but alas, he arrived. It was okay, and when I say okay, I really mean it was meh.

The few funny moments were completely cancelled out by the inappropriate questions that proved he was probably too much of a jackass for my liking. He was also shorter than he said on his profile, so, yeah, ugh. When he walked me to the car he went in for a kiss. I dodged it masterfully and instead delivered the most majestic high five of my life. The crowd cheered at my agile and victorious performance. I had another date the following night, which was another first dates disappointment. I did, however, confirm that if the dude is wearing sunglasses in all his pictures, there’s a chance he is a pirate.

For the love of Tinder

I have made some new and special friends during the first dates interview process:

1. Aquaman with the dad bod, who promises he will end my streak of no second date by taking me to dinner AND drinks, in the SAME night, before he ghosts me.

2. Captain Sadness, who can’t stop telling me about how much he misses being married and can’t wait to have a new mum for his kids.

3. Mr. Toughguy, who says, “if you’re a feminist, you’re paying the check and I’m getting two appetizers.”

4. Chief Bot, who obviously is a robot using some extremely attractive man’s stolen internet headshots.

5. The Counsellor, who wants to talk way too much about my dead husband. And, of course,

6. The guy who asks if I can come over, right now, at 2am.


Are you dating in your 40s at the moment? How are you finding the first dates? Leave a comment below and follow us on Instagram here where we’ll be keeping the conversation going.

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