The 3 Worst Dates I’ve Ever Been on as a Digital Nomad

Be careful out there, folks. I’m about to tell you about the 3 worst dates I’ve been on since I began my digital nomadic odyssey.

These stories are funny to me now, but at the time I was less amused. Don’t worry–nothing terrible happened, but still, look out. The last one is the absolute kicker.

Ready? Let’s get to it.

Part of the Cathedral of Junk in Austin. It’s kind of similar to dating–lots of junk out there, but you might find something good.

Bad date #1: Rat Boy

I met Chuck (not his real name) off a dating app. Not a nomad app, just a regular dating app. We’d agreed to meet at a coffee shop after barely messaging each other (never a good idea, IMO).

By the way, I advertised that I was a digital nomad on my dating profile–I think it’s best to get that little tidbit out in the open right off the bat. Chuck seemed interested in my life of caffeine and Wi-Fi and fancied himself a traveler and nature enthusiast, like me.

Well, I got there and he didn’t seem particularly thrilled to be there. I get it, dating sucks. But he didn’t even walk up to the counter with me to order, which I thought was odd. I got a bloody mary (it was a New Orleans coffee shop) and some beignets, which I offered to share.

“In a little while,” he said.

Then he talked at me for a solid 30 minutes or so. I couldn’t get anything out besides “Oh, interesting” or “Wow.”

He talked about hiking, camping, and taking psychedelics with his friends. All things that I find interesting. Except when this guy spoke about them.

How could anyone who uses psychedelics be this boring? I thought.

Once I could finally get a word in, I again offered him a beignet.

“I already had a bite,” he said.

Somehow, when I must have looked away for a brief second (or maybe I nodded off), this dude had managed to take a bite of my beignet, just the corner of it. Like a rat had nibbled on it.

Dude, I would have cut you off a slice.

I looked from beignet to him and him to beignet.

It was kind of like having someone steal a fry off your plate, but imagine if they’d just taken a bite out of a fry and set it right back down. And you didn’t even see it happen. Yeah.

“Oh,” I said.

Then, as my stomach started turning, he continued talking at me like nothing had happened. And I politely listened. I’ve never had the guts to just ditch a bad date. But there wasn’t a second.

A swirly margarita from a solo “date,” which is what I should have gone on.

Bad date #2: The dude who ditched me after 10 minutes

I really have to hand it to this guy–he had the guts to GTFO stat. I should be more like him.

I’ll call him Justin. We’d had a promising conversation over a dating app. He was a hiker too and had done the Pacific Crest Trail. That trail takes months to hike, and at 2,653 miles long, it’s a bucket list item for sure.

He also told me about a digital nomad he knew who had hiked it. She found places along the trail where she picked up cell service and worked off hotspot during the days and spent evenings hiking further.

Of course, it could have all been bullshit.

Justin and I agreed to meet at a festival. Pro tip: do not have a first date at a festival! The whole point of a first date is to get to know each other, and it’s impossible to have a conversation at a festival!

On the way there, I wondered if he’d stand me up… then I began HOPING he would stand me up so I could enjoy the festival and do what I wanted to do. After all, I didn’t know this dude, and I was so used to flying solo at festivals and events that it felt a bit weird to be meeting someone there, especially a first date.

When I spotted him, there was just something about him I didn’t like. I can’t quite put my finger on it. Maybe it was the almost mirrored sunglasses he wore. Maybe it was the way his tank top hung on his sunburnt shoulders. Maybe the flip-flops he wore on his feet. I don’t know. But I awkwardly introduced myself anyway.

We walked and talked. We went down rows of tents with festival food, drinks, and artwork. It was hot and crowded. We pushed through people like we were in the birth canal, him leading the way and looking back at me every now and then, me nodding my head, pretending I’d heard what he’d said. 

We found clearings here and there to have pieces of conversation. He’d pause at things that I was supposed to be impressed about.

“I’m going to go home later and…get in my pool…”

I needed a drink.

I paused at a tent and got a beer. He explained to me that I could get a souvenir cup for a buck more, which I believe I later gave to my mom.

Then of a sudden, as soon as I’d gotten my drink, he announced he wasn’t feeling well and went home.

To his credit, it was very hot that day, and he said he’d been drinking heavily the day before. Maybe it wasn’t a lie. But. We never spoke again.

So I got my wish. I enjoyed the festival solo, like I do everything.

Bad date #3: the dude who wanted me to save him

Now for the kicker…

I was at a brewery in Austin, TX solo. And I met a man named…well, we’ll call him Fred.

I was talking with someone at the bar and told him I was a copywriter. Then his face lit up and he got the bright idea to introduce me to his friend “who’s also in copyrighting!”

The legal thing, not writing copy.

He brought his friend over, and we hit it off right off the bat.

Fred was only 31 years old but had wrinkled early because he had a permanent look of incredulity on his face. Imagine a grandma who was always amazed at everything you said and just couldn’t quite believe it.

I found the wrinkles charming. Like Clint Eastwood.

Somehow we managed to skip all the small talk, which I as an introvert, loathe, and we went straight to the big stuff—life, God, psychedelics, the afterlife…

Whoa…

It all started off very promising.

He had a PhD in some kind of engineering. Civil, maybe? He’d moved to Austin a few months ago and was working at a law firm dealing with some sort of copyright shit.

Don’t ask me how it all fits in…

He’d needed a fresh start and decided to find it in Austin after, I gathered, chasing after an ex who’d moved all over the country, most recently to Arizona.

When I asked for more details, he just looked at me, lowered his eyes, and said “You’ll find that out later. Not right now.”

Now, alarm bells may be going off in your head. And they were in mine too, but I also love a good mystery. I was hooked.

The night went on and Fred was perfectly pleasant. I told him I was planning to go to Chicken Shit Bingo the next day, and he was excited, said he’d never been but would love to go with me. So we already planned a second date when we were kind of on the first.

I couldn’t place his accent. He looked vaguely Indian but did not speak with an accent I’d ever heard before. It turns out he was Indian…but it was like… California Indian. Slower and more mellow-sounding. I guess that’s what happens when you chase exes all over the country.

I fell even harder when he bought me a taco.

One of the many great things about Austin is that there are taco trucks everywhere, and outside the brewery was no exception.

I told him I’m pretty much always hungry (true).

He told me to be sure to tell him when I got hungry again. Then he preemptively bought me more tacos.

I was crushing hard, and we made out in front of picnic tables filled with unsuspecting folks who were just trying to enjoy their tacos.

I told him about a piano bar I’d heard of downtown, and he’d heard of it too but had never been so…that seemed like the logical next spot to hit.

We got in an Uber and rode off into the sunset. The sunset being “Dirty 6th” in Austin.

And sometime during the Uber ride, we started talking about tattoos. Now, it gets chilly in Austin in January, and I had on a jacket covering my sleeve. He told me I “didn’t seem like the type” who’d have tattoos and asked how many I had.

As we were getting out of the Uber I told him 3.

“How many will I see tonight?” he asked.

Ooof. Forward.

“One,” I replied, “because I’m going to take my jacket off at the piano bar.”

During the Uber ride, he’d gone on and on about some sort of whiskey drink he wanted me to try, so he ordered me one when we got to the bar.

While we waited, he kept staring at me. I was feeling a bit uncomfortable, but it was about to get worse.

The pianist was playing “Wonderwall” by Oasis. Now, Fred and I didn’t grow up with the same things due to cultural differences, but that was one song we both knew.

And he looked at me, made the most intense eye contact when the chorus came on, and sang directly to me:

“Because maybeeee…. You’re gonna be the one that saves me….”

It was something about the way he looked at me. His eyes, the way they pleaded through those wrinkles. Like I was the lifeline.

Shit.

“And after all, you’re my wonderwallllll,” he crooned.

I smiled awkwardly and deflected by asking him what a wonderwall was anyway. He didn’t know.

By the way, the whisky drink turned out to be a normal old-fashioned. Nothing special.

I was feeling uneasy but sat down anyway. There’s a part of me that’s morbidly curious. Sometimes this manifests itself as “Fuck it,” and “If you can’t beat em, join em.”

We sat down, drank our whisky, and talked some more. I noticed something peculiar. Any time I’d pay attention to the music instead of him, he’d pout. I don’t mean that he’d literally stick his lip out. But he acted sullen and jealous.

He tore my attention away from the piano music and made out with me some more. But after he tried to shove his tongue down my throat, I revived the conversation.

We asked each other basic questions about music tastes, movies, and traveling. He pretended to be excited about everything I said. My bullshit detector was going off, so I decided to test him when he asked what my favorite movie was.

“Harold and Maude,” I answered.

“Really? I love that movie!” He moved back in with another super aggressive kiss. I pulled away.

No, he didn’t love that movie.

“What’s it about?” I asked.

He thought really, really hard about that. His wrinkles were fully creased as he pondered. He put his head in his hands and you could see the “Oh shit” pulsing through his body.

Finally, after a way too long pause, he said, “Is that the one with the dark forest?”

No, it wasn’t.

But I was somewhat amused at his answer. A dark forest?

If you’re gonna lie, at least lie big.

I mean, I’d given him two characters’ names already. Come on. Make up a story about them. Or pretend to confuse it with Harold and Kumar. Something.

It was then that I started thinking about my exit plan. I know, I know. In hindsight, I should have planned it much sooner.

If he was embarrassed at being caught in a lie, he did a damn good job of hiding it.

He kept talking, mentioned me coming to India to meet his family.

And that led him to asking me to sleep over that night. “You can have the bed. I’ve been wanting to sleep on my couch anyway to see if it’s comfortable.”

Nahhhhh…

“I better get home to my dog,” I said and got up to leave.

He followed me out of the bar to lively Dirty 6th where I ordered an Uber.

He went on about how maybe he overstepped some bounds, how if this wasn’t a first date, he’d insist on another date.

I really didn’t want to hear any more.

Then I got to use a line that I’ve always wanted to use, thanks to Seinfeld…

“It’s not you, it’s me.”

I got in my Uber and rode off into the sunset. The sunset being the room I was renting with my dog, L.G.

Somehow Fred and I hadn’t exchanged numbers that night. So I never heard from him again.

I went to Chicken Shit Bingo the next day, head on a swivel. I wasn’t going to let him ruin my good time.

But thankfully he didn’t show.

A chicken at Chicken Shit Bingo in Austin

What about you? Got any dating horror stories?

Share them with me below in the comments!