Yes, I Keep Going on First Dates and I Think This is Why

Some days, I am so over first dates. And other days — well…

I am so over unintentional men who just play around with your time and energy–that is, if you let them. For the first time in my life, I’ve broken my record of dates I’ve gone on in the span of one year: 1.

I’ve been on over 10 dates in 2019 and the year is only halfway through! This is actually a big deal for me, so excuse me while I do a little victory dance for getting out of my comfort zone and doing new things. Out of those dates, six have been ‘first dates’. Some exciting, some not so much. Some promising, some — well, not so much.

Y’all, it’s really rough out here.

But this is old news and also frustrating echos that, as a person stuck in the perpetual cycle of singleness, I’ve voiced over and over to my friends over a few drinks at wine and cheese night. Sometimes it feels like no one knows how to date anymore, or rather, no one wants to put in the work to date well — while still expecting good outcomes to come out of mediocre effort.

So then, why do it at all? You might be asking me as a married person who’s been out of the dating scene for years, or maybe you’re like me, trying to ask yourself the same question.


Practice makes…better.

Maybe because I’m in the midst of job hunting post-Masters degree while also trying to jumpstart my romantic love life, but sometimes dating and job hunting feels eerily similar.

Nervousness leading up to the big day.

Putting your best face forward in hopes that a connection of some sort will form.

Learning more about who they are and sharing who you are to find out if you’re a good fit.

And if all goes well, you may just get a second intervi — I mean, date.

Like interviewing, dating can be intimidating, energy-sapping and discouraging if it goes on long enough. But with every “interview” I find myself feeling more at ease in my own skin and confident in knowing who I am — and because of that, I am unashamed to be entirely myself around my date with the hope that they will get the chance to really see me as I am.


Dating is one of the few instances where you can unabashedly share who you are and let another person do the same.

I mean, the whole point of a first date is to get to know someone else — maybe they love going to farmers markets on their days off, or hiking on overcast mornings to catch a breathtaking view, or walking the belt line to meet all the cute dogs (guilty) — and it’s one of the only spaces where you can authentically share about who you are and what you’re looking for out of life. Where you can be known, and let others be known too. And as a type four on the Enneagram, that’s the best feeling in the world.


I’m still hopeful that he’s out there. And I can crone on and on about the plight of being a single woman out in the big bad world of dating, but it won’t get me any closer to finding a partner who I feel like I could spend my life with. And I do hope I find him. He’s the biggest reason I keep going on these first dates after all.

Sure first dates can be awkward but I can’t give up on them.

Though admittedly some days it’s tempting. It feels like this cycle of swiping, matching and dining will never end. Don’t get me wrong, I enjoy going out for a nice meal just like anyone else, but the hope is that one day, one of these first dates will be my last.

Until then, you can find me doing my best not to hurl my phone at the wall opposite my chair after yet another round of swiping right and left. I’ll be here, trying my best to figure out this complex and ever-changing puzzle that is dating in 2019. Wish me luck.

Written by

social worker. aspiring radical doula. dog aficionado. a girl with a lot of words in her head and not enough space to store them.

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