Check please!

Dating stories to spit up your beer to

Apr 26, 2024

Hello friends and readers. All this week CBS News—beginning with a CBS Sunday Morning segment on the 21st—is featuring stories about online dating scammers. Experts estimate that fully 25-30% of all Match.com profiles are nefarious and seeking to lighten a lonely heart’s wallet. Let me say first that I’ve known a fair amount of people that have successfully used dating apps to find their special someone. A lot more people I know have used them to hook up briefly.

For me—Match.com was an unmitigated shit show and carnival for dishonesty. I also briefly used a Matchmaker who freely admitted that the main draw of men for her service were guys that wanted to sleep with her—as was indeed my case. That didn’t happen and neither did any less-than-weird dates.

These snapshots are a look back—to a brief time when I tried online dating—shared with honesty and humor from a now happily married place. As you may know I got married last December for the first time at age 65. Most of my friends didn’t think it would ever happen—but I finally leapt into a sacred marriage bond with my best friend Ann. And NO we didn’t meet online.

I’m sure those of you that have dipped into the online dating pool have some equally absurb and funny ones. Maybe it worked out for you? Feel free to share in the comments. This exercise of sharing my adventures was stimulated by another author here on Substack—a comic named

Rosana S

who has written about her humorous speed-dating experiences. I promised I would share a few months back so I’m making good on that promise. Enjoy.

First a disclaimer. My history was that of a serial monogamist. If I was with you—I was with you. I’ve had some wonderful romances. I’ve also had some long-term play date and travel partners—good times and low expectations. I’m grateful for all. The period of time that I’m about to describe in vivid—and hopefully humorous—detail was a period of about 8-10 years in my 40s. I had a small entrepreneurial company with a business partner—tons of stress—a solid drinking and drug habit—an inflated sense of self that could be popped with a pinhead.

I’m not proud of it but my dating approach was full-on Death Cab Cutie:

You gotta spend some time, love
You gotta spend some time with me
And I know that you'll find love
I will possess your heart

I was a card-carrying member of the 4H Club of single men. Hook up. Hook set. Heart won. Haul ass. I’m a living example of the change possible through sobriety and living an examined life. I thank the Lord daily that I didn’t find what I thought I was looking for—at least not for very long.

Karen (swear to God) was supposed to meet me at 7 pm for drinks and dinner. Given my history with Match.com dates thus far I had recommended a place where I could comfortably observe everyone walking in the front door of the Cherry Creek North (Denver) establishment. It was now my go-to place for first Match date nights. From the end of the bar—adjacent to the door to the patio—and a quick escape if necessary. As 7:20 approached I reached to finish my second Johnnie Walker Black double rocks with a twist. Just as I was getting up to leave—20 minutes is plenty—I saw a woman enter who resembled Karen’s Match photos. My right leg pointed to the patio door. My left leg paused for a just a beat—and I followed it to the front door to greet Karen.

Bad left leg. Bad!

I introduced myself. Karen began with a litany of apologies about parking and feeding her cats and changing her outfits. We were seated. Let me first say that there was something about her that made me want to entertain a first date. She was clearly bright—and committed to her work—and she loved the outdoors. As we were seated I quickly ordered another drink while she held the attention of the waiter for a full 5 minutes discussing the various meaningful attributes of the white wines available by the glass—finally settling for a New Zealand Pinot Grigio from a screw-top bottle. Cuz—corks—you know.

Karen launched back into her discussion at the door of her difficulty with parking. I mentioned that there is valet parking. Oh no I never use valets—I’d never give anyone else my keys.

Okey-Dokey. I didn’t actually say that out loud—because that would mean interrupting—which was a part of my personality that I was trying to be more cognizant of and reign in. She was rollin.’

Next she described how feeding her cats had taken a bit of time. I asked how many cats? She said well currently I have nine—I just lost my oldest girl. It’s abundantly clear why that little nuclear fact wasn’t in her Match.com profile. Karen then launched into how each cat eats differently so she has to take time to prepare and place the variously sized kitty dishes around the house appropriately for each one—because you know—that’s the way they like it.

Check please!

I wasn’t sure which direction I wanted to take the conversation—but any of the other 359 available degrees would do. Alas I had no hand on the rudder. She continued—shifting gears to describe her meaningful work as a lawyer. While missing that vital inhale that is required by most human beings—Karen shifted breathlessly into her wardrobe decision for the evening. I work at home so I don’t get out much except for the rare meaningful client meeting and—you know—the store and stuff. The word meaningful was apparently one of her only retrievable adjectives.

Check please! None of the critical lifestyle information that I’d been receiving from Karen in the last few minutes was outlined in her Match.com profile. Imagine that.

The waiter came around 15 minutes later to take our order. I seized the opportunity to get a word in edgewise—we won’t be having dinner tonight—just drinks. Ordering another JWB I mentioned that I needed to use the restroom. She looked at me with a panicked look and said Please don’t leave. To suggest that the thought hadn’t crossed my mind already would be dishonest. But I said I’ll be right back—I need to use the facilities—to poke out my eyeballs—to snort an 8-ball—to drown myself in the toilet.

I came back sat down paid the bill said my goodbyes and was on my way. Sparks flew and rubber burned in my wake.

Andrea met me at a dinner spot in Cherry Creek North that she’d picked. Her profile was loaded with the love of complimentary activities to mine—skiing and mountain biking and golf and travel. She had lived in Aspen at the same time I had lived in Vail. When we met there was instant chemistry. As our dinner unfolded, we discovered many other things we shared a love of. Then she started talking about her Match.com experience. Uh-oh. She mentioned the last guy she had dated—a local dentist. As she told the story her voice began to rise to shrill levels. She said that she had broken it off because he’d been cheating on her—with another Matcher apparently. She went to his house—to which she had never been invited—he had forbidden it because he was married. Oh boy. So lemme get this part straight in my head—he was cheating on his wife with you—and you’re mad at him for being with yet another Match.com hookup? As her voice was peaking, she described how she had stormed off his front porch and then gotten her own car keys and proceeded to scratch the sides of several cars parked in his driveway. She said I got him good! with great glee.

Check please!

Literally as she was concluding that story—and I was looking for the waiter to ask for the check—she looks over my shoulder towards the front door and her eyes go wide. She lowered her head and whispers to me that’s him! A group of 4 men walked across the restaurant and were seated at a table in the back. Without being too judgy let me just say that this group of oversized combovers was not much to look at. Not a one of them. Andrea’s entire demeanor changed to angry and hostile. As I was rubbernecking around for the waiter—she said to me I’m going to the bathroom and fled the table—right past the table of ill-dressed insurance salesmen in the back. Thankfully I managed to wrangle and pay the tab while she was gone. Upon her return she settled in at the table—and once again her countenance had changed back to the smiling woman I’d met upon arrival. It wasn’t him she mentioned. Oh well that’s good I blubbered. As if that was the issue.

Check Please!

When you’re single your friends consider it their sacred duty to be matchmakers—particularly the married ones. Gosh you guys what do you imagine that Betsy and I have in common? The first response—always and forever more—well you’re both single. Then usually a grope for another thing or two. You both like dogs. You both have a job. And you’re both our friends. Thanks for reaching deep on this one you guys. Never mind. Betsy and I will just have to continue to suffer in our loneliness and miss the relationship bliss that you two are so obviously enjoying.

Every once in a while I’d take the bait.

Nina was another attorney introduced to me by a work colleague. Nina was tall and dark and fancy and mysterious—at least according to my colleague. We’d only met for a couple of dinners—not yet time to reveal the cray-cray. I had a week-long trip to Kauai coming up with my good married friends Adam and Analisa. Being the rarely sober—and always impulsive man that I was—I spontaneously invited Nina. What are you doing next week? Wanna go to Hawaii on Saturday? She looked at me with her best prosecutorial stare and replied Sure why not?

Why not indeed?

So off we went to Poipu. The first night—sleeping in two double beds in the guest room Neener-neener awakened me about every 15 minutes. You’re snoring and I can’t sleep. OK now neither can I. After about 5 interruptions I finally moved to the couch in the living area of the condo. The next morning over coffee she offered I didn’t mean for you to sleep on the couch. Hmm…what other solution would you propose my legal-minded friend? She had none so the couch it was for the week.

Later that very day we were all packing up for the beach. All except Nina who apparently needed her co-counsel’s input to make her beach packing decisions. Will it be hot? Do I need a change of clothes? Where will we be going after the beach? After much discussion about our proposed—and supposedly spontaneous schedule—and much eye-rolling—Nina overpacked her backpack to her satisfaction and we were off. Fun ensued all morning with frisbee play and body surfing by the three of us. Nina meanwhile was appropriately covered up—applying sunscreen—flipping over like a piece of bacon in the pan—and adjusting her headphones—book—sunglasses—towel every few moments.

Dressing for lunches and dinners was an exacerbation of the first morning’s opening statements. Jury what say you? The little black dress or the floral pants suit? Hair up or down? Flats or heels? Quickly my friend Analisa leaned in and asked how it was going with Nightmare Nina? The private nickname stuck. She proceeded throughout the week to question everything. Objection! On our final day we were supping at the elegant Grand Hyatt Kauai. I had on my sleek pair of Tommy Bahama black silk shorts and a matching white silk shirt. At one point she actually came over and sat on my lap and whispered in my ear; this is really nice—but you really should’ve worn slacks.

I took a brief walk around the property—passing twenty or thirty well-dressed men in shorts—and called the United Premier 800# on my flip phone—this was pre-smartphone days. I was able to secure Nina a separate flight back to Denver through LA rather than the one leaving an hour earlier through San Francisco. I had paid for the ticket after all—well within my right to make the change. After we all settled in at the Lihue terminal for our red-eye flights home—Nina asked about our seat assignments. It was there that I said well you have a Premier seat for the 10:45 through LA. I have a first-class seat on the 10:00 through San Fran. At last there was silence. No rebuttal. No question. Just a look—not of hurt—but of pure fury. She marched off to her appointed gate and I never saw her again.

Looking at each of these adventures reminds me of the definition of insanity. I was a mess—hiding—or not so much—my full-blown alcoholic behavior. Yet I was judging each of these women as the ones that were incompatible. If I was honestly looking for a life partner match during those days—I’d have been seeking a dishonest drunk. To thine own self be true as they say. I wasn’t capable at the time. Instead I sought someone who actually had their shit together and I judged them quickly and fiercely if they didn’t rise to my unreasonable expectation.

On with the fun!

I awoke at approximately 2 AM to find Christa standing over me. Fully dressed. I can’t sleep. No shit—you never can. Maybe it’s all the Adderall you’re chomping? This dating experience had progressed a bit—my first one since I had gotten sober a year before. My AA sponsor at the time had a long conversation with me about dating in my first year of recovery. He said look I know I can’t ask you to not hook up. But I’d suggest not giving any house keys out—and always check the purse and medicine cabinet. This from a guy who was currently in his 5th marriage.

I had looked at him and said wait I’m working on trusting my choices more—how does it fit with that to be going through my date’s purse and peeking in her medicine cabinet?

He replied in this instance trust me—there’s a lot of forms of sober—and you wanna make sure you’re not dealing with some underlying mental health issues that might slap you upside the head later on.

This was my first attempt at sleepovers since getting sober. Christa and I had fun together. Movies. Long walks. Meetings together. She liked my dogs. After a few weeks of intermittent dates and sleepovers I noticed that she just didn’t sleep. Ever. Huh…

One evening I got a sneak peek inside the mysterious and cavernous space know as a woman’s purse. Right on top were 5-6 prescription bottles. I didn’t get far but I did see the name Mydayis on a couple of them. Not being familiar with the substance I later Googled it to find it to be a trade name for a combination drug of mixed amphetamine salts. There were more but I didn’t need to keep looking.

That night as she’s standing over my bed—and I’m looking at her hands for sharp objects—she announces I’m leaving. After dead-bolting the door behind her I head back to sleep. That. Was. That. I’d see her at meetings now and then but my go-to was a daily 7 AM meeting which was rarely convenient for her night-owl schedule.

Sargeant Moore from the Denver Police Department called me at my office on Tuesday morning at 10. I’d like to ask you some questions about your girlfriend Shauna. Could you come by the station today?

Uhhh…sure. I thought I knew what it was about. I actually had no idea. Shauna and I had dated for the maximum allowable term—90 days. She was fun and just as crazy as I was. One of our first dates was to a Denver Nuggets NBA game with my business partner Jason and his wife. Unbeknownst to us it was high school cheerleader team night. During each break a different HS cheer team would take the floor for a quick routine—then at halftime there was a montage of several of the teams performing. Ready? Ok. Yay.

At some point just after the halftime glee show our dates disappeared to the restrooms. Shauna had already been busted throwing peanuts at a loud guy a couple rows in front of us. Jason looked at me and said she’s a pistol—where’d you find her? I told him that my good friends Darrell and his brother Waldo had recommended her to me a few weeks back. A few minutes later Shauna came bounding down the steps and breathlessly asked me for my wallet. I need to buy something. I complied. Half hour later Kristin—my partners wife—came back down and told us what Shauna was up to. She’s buying a cheerleading uniform off of one of the HS teams. The Moms are very pissed and it has turned a little nasty. Before I could even react and head up to the mezzanine—here came Shauna—fully dressed as a Highlands Ranch HS cheerleader—pumping her arms and cheering Go Nuggets! She proceeded to plop down next to my incredulous stare and hand me back my wallet. What do you think? It only cost me $200. I stammered in my surprise its uhhh—kinda hot.

The rest of the game was a blur as one mom after another came down the aisle and stared at us until someone griped and shooed them away. At the end of the game we were confronted on our way out by a full HS cheerleading team—all the moms—and a Denver cop. A heated discussion ensued whereby the cop eventually calmed the moms and asked the one cheerleader who was now out of uniform if she felt she’d sold the uniform fair and square. She defiantly said you bet I did. End of story as far as the cop was concerned and we were on our way—my 40-something cheerleader bouncing her way out. The night at home was fantasy material—what with a cheerleader uniform and the victorious spirit of my own cheer captain.

So of course I invited Shauna to fly to St. Maarten with me in two weeks to spend a week on my buddy Andy’s yacht. Some of my closest friends were aboard and this was their first introduction to the spirit that was Shauna. It quickly devolved. We were moored in the harbor of St. Bart’s and that required taking a tender in to shore for all meals and excursions. Every single time—despite my pleadings—Shauna would be a full 30 minutes late to the deck for departure. After three or four of these the group began leaving without us—requiring the crew to make an additional roundtrip for the two of us each time—then just for her as I began leaving her behind. We managed to not throw her overboard during the one-week trip and everyone made it to the airport in St. Maarten. Despite my attempts at re-routing another date’s trip home from a vacation—I was stuck with Shauna for a trip to NYC to join Jason and Kristin once again for a prestigious industry award for our young company. Tavern on the Green was filled with black ties and little black dresses for the annual PR WEEK Magazine’s awards. To say that we were underdogs among this elite crew of PR and Communications agencies would be to understate it. Despite the odds we were awarded the 2004 PR WEEK Innovation of the Year for our proprietary online mediaroom software.

At one point early in the evening—prior to our award announcement—and following several bottles of good red wine—Jason quietly asked me how the island trip had gone. I rolled my eyes and whispered shit show under my breath. With Clayton Kershaw-like precision Shauna drilled my tuxedo with a full glass of ruby-red Argentine Malbec—stood up—and fled the room. In a somewhat prescient wardrobe selection—I had chosen a dark maroon vest. After a quick pat-down Jason and I and our invited guests celebrated the unexpected award—met some potential channel partners—and changed our company’s future.

I fully expected Shauna to be gone when I returned to our room at the Park Plaza but there she was—crying hysterically—with bags half packed on the bed. The rest of the weekend was muted for her—celebratory for me. There wasn’t any coming back from this travel adventure. This time I managed to create flight separation for the trip home to Denver.

Then came the call from Sargeant Moore. The questions would be few and brief. I didn’t need an attorney present. I had no idea what was going on—but I knew that I hadn’t broken any laws as far as I knew.

SGT: Did Ms. Boswell ever discuss her workplace or her employer?

ME: Sure. As far as I know she enjoyed it. She invited me to the Christmas party a couple months back. I met her boss and her colleagues.

SGT: Did she ever give you anything of value? Money? Jewelry? Art?

ME: Hmm…yes she did. She gave me a wonderful birthday gift last month. She told me she’d commissioned it with a local artist. I thought it was excessive but beautiful.

SGT: Do you still have it?

ME: I do.

SGT: Describe it please.

ME: ‘Bout a foot tall brass statue of a female human figure with a small diamond heart in the outstretched palm.

SGT: That fits.

ME: Fits what?

SGT: I can only say that it would be in your best interest to bring the statue to us immediately as it is evidence in an ongoing criminal investigation.

ME: Right away officer.

And I did. The story was revealed to me over the next few hours by the attorney representing Shauna’s (former) employer—a commercial real estate developer. She had been their Comptroller for 8 years. She had been arrested on Monday morning as she showed up for work. They had spent the two weeks she was away with me to do forensic accounting. She was being charged with embezzlement and theft of company funds.

I actually got a hostile call from her boss accusing me of being in on it. He was on speaker phone from his office and I knew he was not alone. I said Bob I’m happy to come over right now and talk with you about this. I knew nothing of any of this and I resent your implication. I don’t even know what she’s being accused of. I just got back from vacation and I’m completely in the dark.

So I went. It turns out that his wife had given him the statue for their 20th wedding anniversary several years ago. It had been stolen from his personal office a couple months back. I maintained my composure and assured him to his satisfaction that I was unaware of her criminal behavior.

I honestly have no idea what happened to Shauna after that. There was a small Denver Post article about her arrest—and I never spoke to her or the Police or her boss again. Bullet dodged.

For a long time I thought I just had a bad or broken picker. I was picking the wrong women for me. The truth is more complicated. We are often attracted to our potential mates for a whole complex stew of reasons stemming from our childhood attachments—seeking pieces we subconsciously feel are missing from our own personalities—and simple lust. One thing I’m fully aware of now is that any relationship I entered into during that period in my life was doomed to failure. My own dysfunction and addictive behaviors didn’t allow space for anyone else to exist. There just wasn’t any room. The entire dating exercise was a childish attempt at filling short term needs.

The women in my stories were real—the names have been changed. They are perhaps now a loving partner or wife to another deserving man—but it wasn’t possible for us at that time in my life. I’m sure if you asked any of those women about their memories of our interaction—they’d either have forgotten them entirely—or have a completely different take on it. Fair enough. This is my essay—so I’m sticking with my humorous and appalling version.

Well, I know it wasn't you who held me down

Heaven knows it wasn't you who set me free

So often times it happens that we live our lives in chains

And we never even know we have the key

Jack Tempchin

Already Gone—Eagles