Six months after my stepdaughter died, I was still grieving and my wife was incredibly sad all the time. After hearing about Compassionate Friends, a support group for parents who had lost a child, I convinced my wife we should attend a meeting. It was awful. We sat on folding chairs in a circle with…
Author: Steve Ainslie
My Wonderfully Boring Life
I think many people would consider my life to be incredibly boring. I wake up early before dawn to walk the dog and then workout for hours. Then I swim a mile, eat lunch and take a long walk with the dog through the woods. My afternoons are filled with chores, drumming, drawing, reading, catching…
Do The Hard Thing First
When I am wrestling in my head with a problem, the answer is often quite simple – do the hard thing first. With dating, the hard thing initially was trying dating apps after years of proclaiming I’d never use them. Within a few weeks, I got past that. The next dating challenge was how to…
Conspiracy Theory
What I miss most about having a best male friend, a girlfriend, a wife or a partner, is being co-conspirators. I miss huddling up in some corner of a crowded room in our own private world – having intense conversations, raucous laughter, whispering off color jokes, speaking our own code words and intimately sharing with…
By The Numbers
I downloaded my dating app statistics from Hinge for the past 3 months so I could take an objective look at the numbers. I “liked” 910 different women. Of these, 14 “matched” me back. That means 1.5% of the women I found detractive enough to contact, replied to me. I “unmatched” 270 women who “liked”…
All Dressed Up And No Place To Go
When dating TMF earlier this year, it became obvious that my “desert survivalist/exercise enthusiast” wardrobe wasn’t going to cut it. On our 3rd date – dinner at a sushi restaurant – I felt like a complete schmuck when I showed up wearing a fleece with jeans and Merrell boots, while she was dressed to kill…
Casual Connections
During the pandemic, I came to understand how much I needed casual connections with other human beings to maintain my spirits. I was grateful for the few in-person conversations I had each week with: The grocery store check out lady The check-in clerk/temperature taker at the swimming pool The neighbors I’d see when I walked…
Ex Familia
When I was growing up, my family was torn apart by divorce, relocations and a house that at times resembled a homeless shutter or foster home. Amidst that chaos, I longed to have a normal family like my friends did. I wanted to have a home filled with loving parents, good kids, a dog, peace…
Dating vs Marrying
When I began dating a few months ago, I was certain I wanted to be in a committed relationship. My dating fantasies included spending lots of time together, falling in love, moving in together and eventually marriage. Why? Because that’s the only thing I knew. I dated a few different women (girls) in high school…
Maybe I’ll Stay Single
Dating, for the first time in 32 years, after a 29 year marriage (plus 3 years of single living after being widowed), has been exhilarating, exhausting, fun and frustrating. The dating app experience kind of sucks. I am constantly the one who has to reach out to women. I have not been approached by a…