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My attempt at hacking online dating

As 2019 prepares to change to 2020 and I see my own personal calendar preparing to switch from 36 to 37 the vexing, dreadful and exhilarating area of dating came back to me. I thought about how I might approach it this go-round as opposed to how at other times. The fact that online dating now feels like the default channel brings both its ups and downs.


  • A nearly endless supply of potential people to review so you can find the "perfect" match. All of this can be done from your couch, work cubicle or while you're in the checkout line at the grocery store.


  • An endless supply of options means people are often reviewed in less than a minute or two (and in many cases much faster). Can we really assess someone well in that time frame?

  • People's busy lives, exhaustion by this process and continuing supply of candidates I find makes an "in real life" get together difficult to reach.

The above and more left me wondering what I might be able to do to find another way. Years ago I ended up seeing someone for a while who I reached out to from out of left field. When I asked her why she'd agreed to it she said the suggestion I'd made for what to do sounded fun and since we had a couple mutual friends felt comfortable committing. So I've decided to try leveraging people I know in a new way because why not.

I've thought up a handful of things I enjoy or have been wanting to try out. The list below is subject-to-expand as more things come to mind and will stay updated here, which also includes all the text under the divider line.

If you're reading this and someone who might be interested to try out something fun comes to mind why not share it with them? If you're a single lady reading this and are thinking, "why not?!" reach out.

This idea came to me as I mulled how I might meet more single women “in real life” because online dating can be frustrating and exhausting. I thought why not create a list of things I enjoy doing or have been wanting to try, share it with people I know and see if they feel like sharing it with anyone they know. 

The rules

  • This is not a date. Just a chance to connect and try something fun together. 

  • We can decide candidly as we wrap up whether this is a one and done, we’d like to be (active) friends or try out an actual date. 

  • For the first get together if monies are involved we’ll each pay our own way to eliminate any tension or confusion. Venmoing (is that a word?) the other person if it’s easier for one person to pay is deemed acceptable.

About me

  • You can get a bit of an idea for who I am via my Instagram feed or my blog

  • If you came by this by way of a friend hopefully that relieves some of the uncertainty around my sanity for trying out an experiment such as this.


  • Ai WeiWei exhibition at the Kemper

  • Ice skating at Steinberg or Kiener Plaza. I own a pair of skates and rarely use them. 

  • Dancing at Casa Loma or another venue around town

  • Check out the Wednesday Night Jazz Crawl

  • Sunday afternoon Bluegrass at Schlafly Bottleworks

  • Sunday Mezcal tasting at the Gin Room

  • If there’s something else you’ve been wanting to try feel free to suggest it

Call (or text) me maybe? 

  • 314-971-6136


Here goes something!

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