Dating Do’s and Donuts: Grown-up Edition


This will age me a bit, but when I started dating back in the mid-90’s, there were no cell phones, pagers where only for druggies, and dating wasn’t high on my priority list. To be honest, it still isn’t. But this wasn’t always the case. A year after my divorce I thought I was ready to join the dating world, even told one of my coworkers that I was going to “put myself out there.” Never had four words haunted me more.

Misconnecting Online

Advice for dating - Online

That coworker of mine decided one late night while drinking wine that I needed to join a dating site. How very considerate of her. After creating a profile of me on a website called OK Cupid she came to work and showed me “my” profile. I don’t know if it was my inability to yell at her at work or the sugar induced a-coma from the Friday donut run, but not only did I thank her, I even kept the profile up . . . curiosity is a dangerous thing.

It only took one date to quickly realize that this particular website was intended more for “hook-ups” rather than long-term commitments. Long story short: the date went home alone and I went home with ice cream.

I learned some hard truths from this short-lived experiment: be wary of what dating site your wine-intoxicated coworker chooses for you. Starting the conversation with “I’m Mormon and you?” to man who had carnal intentions can lead to a very short, disappointing (depending on whose point of view) and very awkward date. More importantly: I was not ready for 21st century dating.

When did dating become such a chore?

Bring on the Baggage

Advice for dating - Ice cream

There’s just too many hoops to jump through now-a-days, especially as a single parent. Really I just want to go the movies, maybe have a nice conversation with an adult and take it one day at a time. Dating in your mid 30’s seems to be more complicated than your early 20’s, especially when you’re being thrown into a dating pool of men and women who also haven’t dated since they’ve partied like it’s 1999: we all just seem so inept.

First off there’s the texting conundrum—it can be useful and easy but it can also be misleading. You no longer have inflections, tone and body language to help you decipher the meaning of their texts, which means you end up making assumptions based on one sentence that had more acronyms than words. “Open interpretation” can be a very dangerous thing. And then there’s that “cell courage” phenomenon where people are more likely to say what’s on their mind via text than in person—which can backfire when you’re eventually expected to talk face to face.

Secondly, we seem to have lost our patience as adults. Before the age of instant-result technology, we would have taken our time to really get to know someone over a course of a few weeks. Now we’re in this rush to find our second chances in love. So let me get this straight: if you don’t feel an automatic attraction to me on our first date then there won’t be a second? Which, if you’re like me, and are terrible with first impressions, you seem to have a lot of first dates and never any seconds: “third” is now a term heard only regarding Hobbit breakfasts and strikes.

We’ll skip the third rant to further emphasize my point stated above.

Lastly, I understand that there is more at stake: we have careers, children and baggage. We have a better understanding of who we are. We now have a better concept of what we want out of a companion, and we aren’t willing to settle, as we shouldn’t. It seems to me, and I can be alone in this theory, that it’s almost easier to remain single than to “put yourself out there.”

I’ve come to the inconclusive conclusion that in the dating world: a walk in the park is no longer a walk in the park.

Some Real-Life Advice about Grown-up Dating

Advice for dating - “Dating bubbles”

So I’ve come up with 5 not-so-concrete, not-backed-by-psychologists (or specialists of any kind), and definitely opinion-based-only dating bubbles that can pop at any moment:

  • Don’t date till you are ready. Whether you’re just fresh from a divorce or your children need more of you, just wait ’till it’s the right time for all involved. How do you know when it’s the right time? Wow, I wish I knew the answer to this one. I personally took the approach of making a deal with Heavenly Father that it was up to Him and that His hand-picked man would literally have to walk up to my door with a huge neon sign that flashes “THIS IS THE ONE.” Lightning bolts would also be helpful. To be fair, I don’t think this deal was ever sealed so…
  • Know who you are and for heaven’s sakes stop molding yourself into what you think they want. You’re no longer a wishy-washy teenager. So when their dating profile says “Enjoys camping, hiking and out-door adventure” and the last camping trip you went on was Scouts/girls camp, and your idea of a hike is maneuvering through Costco on a Saturday—just say no. There’s definitely room for compromise and learning new things but pretending to be a fly fishing enthusiast just because you watched “A River Runs Through It” (more like a Brad Pitt enthusiast, am I right girls?) doesn’t better your odds at impressing him/her. Be yourself from the start.
  • Don’t let the dating process take over your life—a partner should add to your life experience not take center stage. Space out the dates and don’t cancel time with friends to be more available. You don’t want to find that you’ve spent all your time on the hunt and no time with family and friends—don’t be that person.
  • Confidence is everything. At this point in the game self-assurance attracts more of the right people better than any lipstick, sports car or job title ever can.
  • Have fun. It really can be that simple.

In conclusion, I readily admit that I’m no expert, a bit jaded and have a tendency to let my sarcasm run amok. Now that you’ve stuck with me through the whole article, was there anything that I missed? What advice for dating or funny anecdotes do you have for the dating impaired? I’d love to hear from you!

Megan is a thirty-something single mom blogger who lives in Portland, OR. She has worked in Pharmacy for the past 15 years and spends her free time free-lance writing for parenting blogs and writing fiction. When in "time-out" (of her own accord) she reads and writes, then reads some more. Her historical fiction novella is available on Amazon The Max Effect.