Glenn piping in Praia da Luz
Glenn piping in Praia da Luz

Moving to Portugal with the perfect man – and it only took 168 first dates

Did you see that movie “50 First Dates”? Try 168! I got divorced 20 years ago and tried that online dating thing. My second date ended up being a serious boyfriend.

After three years, I was wondering whose house we would move into when he dumped me for a younger, blonder woman with bigger … teeth. I jumped right back into online dating. After all, he was number 2, so it couldn’t be that difficult, right?

After I passed number 25, I started keeping a spreadsheet with a few facts and usually a nickname. Truthfully, the awful dates were the most fun after the fact. Great cocktail party stories. Like “Little Hands”, the guy who could barely pick up a beer mug. Or “Milky Eye”, the guy I couldn’t look in the face. “Grandpa” could barely walk and was falling asleep in the restaurant. “Billie the Kid” told me he liked his women “experienced”.

When I hit first date number 50, I had an epiphany. All these loser guys and terrible dates had one common denominator – ME. Yikes. What was wrong with me? I started asking my friends, but I couldn’t get any good answers other than I was “too stressed” and “too intimidating”.

I re-wrote my dating profile, removing that annoying Vice President title, the pictures of my boat, and those exotic travel adventures. I got a lot of dates, met some nice people, and even had a couple of short-term boyfriends, but “Mr. Right” became “Mr. Next”. There was “Fatso” and “Grumpy” and “Hot Doc” – I was starting to feel like Snow White dating the 70 dwarves.

Number 89 was my only Nut Job. He asked my favorite color and bought a turquoise shirt for our first date (what if I’d said mustard yellow?). He invited himself out with my friends for date two and proceeded to buy everyone drinks all night and tell them how he was “falling” for me.

Too weird, so I decided to gently end things on date three. The restaurant crowd was entertained when he pounded his forehead on the table and started screaming that I was a “” who “led him on”. He followed me out, swearing the whole way and then tried to block my car in the lot.

Glenn and Glenda in paradise
Glenn and Glenda in paradise

The psycho rode my bumper the whole way to the nearest police station. I had never given him my address, but I was terrified that he would hunt me down. He never showed, but I had a few scary weeks.

By the time date 100 rolled around, the years were going by, and my new dates were often grandfathers. And, boy, were they into it. When I would mention my dream of living overseas, they would look at me like I was a lunatic. Didn’t I want to raise my grandkids someday? Well, in a word, no. I don’t have grandkids and if I ever do, I will be the fun grandma with the pool in Portugal.

After I picked Portugal as the perfect retirement location, I thought I could never meet an American man who would move there with me. So, I spent a few winters in Portugal and tried dating here. I met a cute Swedish guy right away. I should have learned to say “bootie call” in Swedish because I’m pretty sure he wasn’t looking for a nice American woman to come home to in Portugal. And I had a date with an interesting British guy, but his nickname on the spreadsheet was “Narcissist Ned”.

So, I gave up. I dated once in a while and changed my retirement plan to six months in the States and six months in Portugal by myself. I was in Florida about to move to California when I happened to see a picture of a guy online playing the bagpipes. An American man in a kilt!

I asked him if he knew of any Ceilidhs in town, and he asked me to come to his new home and help him hang pictures. Unusual first date, but I like to decorate, and he had a dog, so I thought I’d give it a whirl (and keep my pepper spray at the ready).

We hung a lot of pictures, walked his adorable dog, and talked about our mutual love of travel and other cultures. As I walked out the door, I said to him: “If this works out, our friends are going to find the Glenn and Glenda thing pretty amusing.”

And here we are, living the dream in Portugal. It was a long haul. But he was worth all of those 167 dates, even the sad and the scary ones. He tells me every day how happy he is to be in Portugal, with me.

He wakes up with a smile, cooks me incredible meals, and fills my days with laughter and fun. He thanks me often for bringing him to the Algarve, a place he is growing to love as much as I do. I wouldn’t be here full time without Glenn. It’s just too lonely to be so far from home by yourself.

I’m guessing you didn’t have to date 167 people before you came to Portugal with the right partner. Next time you want to push their face in their Cornflakes (Weetabix?), think about “Milky Eye” and “Nut Job”. It’s a jungle out there, and you’ve got paradise right here.

By Glenda Cole
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Glenda Cole retired as the Vice President of Marketing and Partnerships for an international luxury mall developer. She and Glenn have created a popular vlog on You Tube called The Glenn and Glenda Show about their move to Portugal. Glenda is working with the CASA Social Club committee and invites everyone to come out to one of their upcoming events (