*Theo, 20 something- Cougar Nay
Pros:
Tall
Fit
Smart
Extremely kind
Super nice smile
Confident but not cocky
Great texter & communicator
Chemistry was there but need to see how it develops
Cons:
Age Gap (Potentially?)
Frat bro (Potentially?)
Jeans & sandals
Ask and you shall receiveeeeee!
The votes are in, and the majority of you guys wanted to know about my cougar date.
A cougar, for those of you that don’t know, is a woman who dates younger men. Which we all know is extremely off brand for me. Mid 30’s is really my sweet spot.
But-
life happens.
Expect the unexpected.
So this is the story of Theo, the 20-something medical school hottie that I met on a hot day in late July.
It all started when I went to the lido with one of my colleagues. To be fair, I normally wouldn’t be in a SWIMSUIT willingly in front of a co-worker, but it’s a popular Lido and we both said we were going over the weekend anyway so we just said whatever we’ll go together. Anyway it was a chill colleague, so… whatever.
So my colleague, (we’ll call him Simone) and I met up at Lido San Domenico, which is an absolutely gorgeous place on the lake in Castagnola. We got brunch… I had pancakes and a glass of white wine because… why not. And I started my absolutely carefree summer day. I took a little nap on the lounge chair and when I woke up, Simone was gone. I got up and walked toward the balcony of the grassy area I was on, overlooking the lake and the floating dock. I don’t know if balcony is the right word. A grassy ~terrace with a fence and stairs so you can jump into the lake. It’s all very picturesque.
The lush green mountains (like giant broccoli) made the lake even more breathtaking. Simone’s sitting on the dock getting some sun. There’s like a bench you can sit on. He sees me and waves, then gestures for me to come in. After my brunch and nap, it was time for a swim. It’s also hotttt in the summer, so I needed to cool down anyway.
I jumped in and swam over to the little dock in the lake. Climbed on and went over to the bench where Simone was. We talked for a while. He complimented my swimsuit and I remember feeling sooooooo insecure. Like unless I’m actively swimming IN water, I usually have a cute over up on. A flowy dress, or an oversized cotton oxford that’s only buttoned up halfway with my bikini poking through. (That little trick is called show the tata’s, hide the tummy. Also… CHIC). But there I was, in my electric blue bikini, sitting on a bench, my tummy surely roly poly, with nowhere to hide. Whatever- I took the compliment and decided not to be such a b*tch to myself, and focus on other more important things. Like how lucky I was to be in such a beautiful place on such a beautiful day. Also, after moments of insecurity, I have a God complex just hype myself up, so I feel like I’m ~that girl!! I’m like woww, the way the sun is hitting my skin……..it’s glowinggg. I love that. It’s giving melanin, it’s giving sun kissed goddess, it’s giving BODY, it’s giving well-fed (?). Idk if that’s a compliment, but we’re gonna roll with it.
Anyway, Simone eventually went back up to land and I decided to hang out on the dock. I got off the bench and went to the side of the dock so I could put my legs in the water and be gently rocked side to side by the ripples. I closed my eyes and lifted my head toward the sun.
Ah…
peace.
Silence. Stillness. I could still hear people having fun all around me. But it was all… muted. Background noise. The main sensation I was feeling was the hot sun on my face. It’s so interesting how you really never know what’s gonna happen next, when you’ll meet someone new. That has to be the best part about being single- anything is possible. A moment of calm can turn into excitement in 2 seconds… and that’s exactly what happened.
I heard a little commotion and opened one of my eyes to ~assess the situation. Just 3 guys laughing… and I think speaking… German? Well that’s nice, I love to see people having fun.
Hm.. one guy is kinda cute…
I opened my other eye. (To assess the situation better).
All three of them dove in (I always find it really cool when people can dive into water bc I cannot do it for the life of me), and swam towards the dock. They were hanging out in the lake, a few feet in front of me. I got a closer look at the cute one. Very tall, lean but muscular, abs, brown flowy hair, nice jaw line and perfect, perfect teeth. His teeth were SO straight and SO white, they almost looked like in those cartoons when someone smiles and a little diamond glimmers off their tooth with that little *ding sound. Maybe I mentally embellished that a bit, but you get what I’m saying ??
Anyway, I was minding my own business and actively trying not to look at him. You know when you pretend not to see the very hot person right in front of you?? Buuuuut I guess I couldn’t help myself and we accidentally made eye contact. Briefly.
I soft smiled and looked in the other direction. Now is this a technique I would 100% use on land, with clothes on and with my armour of makeup on? Yes! I would one hundreddddd percent use the quick eye contact, smirk, and look away method to hook a guy. But like I said before, I wasn’t feeling the MOST confident. I did not want to hook this fish. At least not in that moment!! Let me put on my oversized oxford button down first, PLZ !!
Too late.
He’s swimming over to me.
shit.
be cool.
Theo: Hope we’re not disturbing you
Me: No! Of course not
Theo: Are you from Lugano?
Me: Um.. no, I’m American… but I’ve lived here for about 7 years, so, it’s kinda like a second home. You?
He didn’t have an Italian accent and most people that actually live in this little city do.
Theo: Oh nice, Lugano is a beautiful town. I’ve just been here a few months. I’m doing a rotation for my medical school so I’m working in an office here. I’m from Zurich.
Medical school!?? A smartie hottie?? I’ve said it before and I’ll say it again, smart hot guys are elite.
Me: Oh so you’re new to Lugano!? And you get to be here during the summer months? You’re lucky! It’s the best in the summer. Are you enjoying it so far? You’re going to all the good places??
Theo: Yeah! I think so! I’ve mostly been coming to the Lidos when I’m off work, but I’ve also been to LUMA.
(It’s a string of bars that goes up right on the lake every summer and thee hot spot where everyone goes).
I told him about a few more places he should try. BTW- he’s just treading water looking up at me for this whole conversation, but looking real good doing it.
Theo: Thanks, I’ll have to check them out! Maybe you can show me some places.
…oh… is Theo shooting his shot?
Theo: Uh, before you leave, can I get your number?
(Sports broadcaster voice) AAAAND Theo Wedontknowhislastname, the Zurich native, standing tall at 6 foot 3, steps up for a three-pointer…
He shoots….
Me: Sure
AND IT’S GOOD!!
Bravo, Theo.
Wow, this is exciting.
Theo: I’m Theo by the way. These are my friends, cantremember and cantremember
Honestly I barely even remember what his friends looked like. (Keke Palmer voice- sorry to this man)
Me: Hi! I’m Nayomi
I waved to his friends.
Theo: So I’ll see you later right? (nodding towards the terrace)
Me: Yeah, I’ll be there (grinning)
He smiled and swam off with his friends like a bunch of mermen. Okaiiii…. that was unexpected. I stayed there a bit longer but the sun was starting to go down and I thought it was time to rejoin my colleague on land, grab an apero and watch the sunset. Simone and I sat on our lounge chairs and sipped on a glass of white wine.
Simone: So, I saw those guys going over to you… are you interested orr? Of course they’re interested.
I just chuckled, shook my head (at the question, not as the answer) and kept on sipping my wine. Theo was on the floor a bit to my right. Him and his friends had their towels laid out on the grass. I couldn’t help but think how confused he must be looking at me with Simone since… well, Simone is a middle aged man and I was there hanging out with him. I could feel him trying to figure me out but I was trying to figure him out too. Besides the two guy friends he was with, he was surrounded by a bunch of girls. Is Theo a f*ckboy? Still to be determined. The girls would move closer to him, show him things on their phones… I mean it was the damn WBNA bc those girls were shooting their shot. And I can’t blame them, he was substantially hot.
The main thing I noticed though was… they all seemed….. kinda… young? Since he was so tall it was less noticeable on him. But his friends, the boys and the girls.. just seemed.. a whole lot younger than me. You know how, well, if you are of a ~certain age- you know how you can just immediately spot the difference between someone who’s 21, 22, 23, 24.. let’s say 25/26 becomes a grey area, and someone who’s 27+. They just seem, act, look, young. Not even in a bad or belittling way, they aren’t doing anything wrong. There are just differences. And well, we all know I prefer a 30 something over a 20 something.
Whatever- it’s not that serious and maybeee he wasn’t even that young! After the sun set, I was ready to leave. I packed up my beach bag and I saw him turn his head. I assume to make sure I gave him my number before I left. But… it was kind of awkward since he was surrounded by a bunch of people and… I had to walk up to him. But I did.
Me: Hey, I’m heading out! It was nice meeting you
Theo: Nice meeting you too!! Here, give me your number.
I had my phone in my hand so I just handed it to him and told him to put his number in.
Me: “Okay, cool, I’ll text you! Enjoy your apero.” He lifted his beer, nodded his head and smiled.
Cute. This guy is really cute. He had a very wholesome energy to him.
I quickly walked back to Simone who was waiting for me at the exit.
Simone: So you were interested, huh?
I shrugged and smirked. No comment.
Simone and I got dinner at my favorite Lugano restaurant, Fermata, and when I got dropped off at home, I plopped myself on my couch, reflected on the fun, and unexpected, day I had, and texted my new friend. Honestly having your own apartment, kicking your feet when you have a new little crush- this is girlhood!
Me: Hey! It’s Nayomi
Theo: Hey Nayomi :)) It was a pleasure meeting you!
Theo: I wasn’t sure how to act, because I didn’t know how you were related to your guy friend ahahha
Me: hahah yeah I get it, but just my colleague 😂
Me: Really nice meeting you too!
Theo: Nice :))
Theo: We should grab a beer/ vino next week!!
Me: Let’s do an apero for sure!
Me: Have you been to Lido Riva Caccia?
Theo: Not yet :)
Theo: Is it nice??
Me: Yes! and on friday they do this sunset dj night
Theo: Nicee
Theo: Looks cool
Me: Have you liked Lugano so far?
Theo: Yes it’s great!
Theo: How about you?
I don’t know if I got tired or just distracted but I forgot to respond to this message. Anyway it was a Sunday night and I had work the next day so I probably just showered and fell asleep.
Anyway, the following Tuesday, August 1st, was a holiday in Switzerland. It was actually the Swiss National day. My incredible, wonderful friends planned for us to watch the fireworks from a boat on the lake, instead of packed in the park like sardines. I love fireworks, I think they are beautiful. After the firework show, we joined the rest of the city at LUMA, which was so full of people it was hard to move. Mixed with the hot, heavy, humid, August air- it was also hard to breathe. But- everyone was in a good mood nonetheless. It’s only natural when you live in a smallish city that there’s a chance you’ll bump into people you know. That chance goes up significantly in the summer.
I ran into one of the UK interns at work, Adam. We caught up on our nights, and he said he was with two of the other interns and some new friends they’d been hanging out with if I wanted to say hi. Of course I did!
We made our way through the crowd and I see the two other interns, give them hugs and say hi.
Adam: Oh, and this is our friend…
Me: Theo !?
Theo: Nayomi!! Hey!
He came over and gave me a hug.
Me: Hi!!?
Adam and the other interns were a bit baffled.
“You guys know each other?”
Me: Umm.. yeah, kind of!
Theo: Yeah we met at the Lido.
Theo: Wow Nayomi!! Such a coincidence seeing you here. Such a nice surprise.
He genuinely sounded so excited and had zero alpha machismo energy, like he had to look cool in front of his friends. (Which- tbh the UK guys had.) He really was so wholesome and cute.
So the girls I was with kind of got mixed up in the crowd and missed the moment where I first saw Theo, so they had no idea we already knew each other. By the time they got to the group, they were like, “Wait, Nay, that one is really cute.” To which I was like, “girls that’s the guy I’m texting!!” (Screams in girl joy). Anyway- we were in the same area for a while but I was talking more with my friends and enjoying the great music that night. We ended up parting ways, I think his friends wanted to go to the casino (.. why? dont ask me.) And my friends decided to skip to another bar. Around midnight I get a text from Theo.
Theo: Where are you @??
It’s cute that he’s looking for me or trying to meet up but.. is this a f*ckboy text? To be determined…
Me: right behind the bus station 😂😂
Me: there’s a random little bar with really fun music
Me: come!!
Theo: We’re at shaker right now
Theo: but its mid hahaha
Me: the music here is sooo fun lol. but it just started raining so we’re coming to shaker
Theo: Great!! :))
We met up and…. Shaker really was mid that night. The vibes were not vibing. Anyway, I’m gonna say something that might be controversial. I generally don’t like when girls get an ick over something 100% normal. Like “allergic to pollen” (I just saw that on a list), or like, makes a sound when they stub their toe. I feel like that’s overly harsh? I mean everyone’s icks are personal so whatever, but idk. Then there are REAL icks, like talking about how much money you have, or being rude to a waiter. So, what I say next, I’m not that proud of, but… I scanned his outfit, and there on the dancefloor of this bar/club… were… full length jeans and sandals. The top of the outfit wasn’t any better bc it was a tank top. I mean he looked very muscular and fit to be fair. But the combination of the tank top, denim and sandals…
I hated it.
I’m sorry!! I HATED it. Tank top with shorts? FINE. Shorts with Sandals? FINE. Tank top with shorts and sandals? FINE- it’s summer.
Tank top with jeans and sandals?? Oh God, my eyes. I was just staring at his exposed toes on the dance floor and having an internal panic.
Let me also just say that this is purely a personal opinion. I’m sure many, many women would have no problem with this. He was kinda giving hippy vibes, and even hot hippy vibes. It just wasn’t for me.
So- whatever- the night was winding down, the bar was closing, and discussions were had about where to go next.
“I think we’re all going back to Theo’s, wanna come?”
Me: (sarcastically) Ooo afterparty? (I had no intention of going)
Adam: ha, I doubt it’ll be much of a party. Last time it was just a bunch of guys smoking and playing video games.
Me: (internal hell no)
Me: So a frat house!? (laughing)
Me: IIIIIIII’m goood. Ya’ll have fun
Listen, I’m not against being in a blunt rotation. But the last time I was in a smokey room with a bunch of boys playing video games, I was literally in college. (11 years ago. Specifically in Pink Building or Panera 5).
Theo: You’re welcome to join Nayomi.
Me: Thank you! I’m pretty tired, I’m gonna head back.
Theo: Okay, we’ll plan something for another time then
Me: Yeah, absolutely! Have fun!
God he’s so sweet. Very kind, gentle energy. Am I really gonna let jeans and sandals block my date? That’s silly.
Being the darling that he is, he texted me the next day.
Theo: How about next saturday afternoon? Lido chill ?! 🤩
Me: hiiii
Me: yesss
Theo: Nicee Nayomii :)) looking forward to it 🤩
He texted me on Friday to confirm our Saturday date. (green flags, green flags).
We were deciding between two lido’s and decided to go back to the one where we met.
Then, the morning of our date he texted me again (green flags, green flags).
Theo: :))!! How are you getting to the Lido?
Me: Hey! I was planning on taking the bus!
Theo: Great !! I think I’ll go by bicycle! See you there :))
I was running late bc I had to quickly wax my legs (UGH- story of my f*cking life), soo I missed the bus, and then I was even more late.
Not great from me. But he was very gracious.
Theo: No stress :) tranquillo
Anyway, besides feeling bad for running late, I was feeling good! My hair had those natural summer waves, I had on a white button down (of course veryy unbuttoned), mini denim shorts, brown sandals, my trusty summer hat, and I think some necklaces. It was one of those days when your hair, skin and outfit all cooperate. Thank God!
So anyway, when you get off the bus there’s a short walk to the Lido. It’s an absolutely beautiful walk. I had some fresh air and time to think. I was excited… and also kinda in disbelief? The last time I did this walk I had no idea I was gonna meet someone new. And how did that even happen? How did I end up here? We always say it’s so hard to meet people in person. Apps are the future. People don’t approach anyone in person anymore. Is that really true? I know it’s less common, but .. why? And what are we doing… or not doing, to attract, or even just be open to an organic connection? Is it our energy? Confidence? It’s not just attractiveness. There are so many beautiful women who don’t get approached. Or maybe they do get approached. Just not by the guys they want? Or maybe they are the guys they want. But maybe those guys are looking to conquer, to chase, but not really to connect, so inevitably it fizzles out. Or maybe, and most likely, it’s intimidating going up to a person and putting yourself in a position to get rejected. Hm.. so many variables. Some that we can control, some that we can’t.
Now that I’ve had some time to process everything, I still can’t say for certain that I have one clear answer. But… what I think happened- at least in this case, is that… the reason he approached me, (besides a baseline attraction which, I’m not pretending doesn’t exist), is because I was in a mindset that was happy, open, and at peace. I was on that frequency. And that’s what I was emitting outward. I think- I really think- in that moment when I stopped being such a b*tch to myself, stopped ripping myself apart for my ‘flaws’, showed myself some love to get out of that negative loop, and then just stopped thinking about it all together, lifted my head up towards the sun, and was just in a state of peace, happiness and gratitude; I am almost sure, that’s when he noticed me. Because- imagine if I was there on that dock- stuck in my own head, face down, looking at my tummy rolls that I wish weren’t there, or checking for the hairy spots that I inevitably miss every time I wax my own legs. Hunched over, crumpled up, trying to hide, focusing on something so stupid, that other people aren’t even thinking about. Is that attractive? Would you want to go up to someone like that?
Of course not. Feel good with yourself first, not just how you look, but how you really feel. Are you happy? Blissful? Content? What’s more attractive than good energy? Positivity attracts, and negativity repels. And this goes far beyond how you feel in a swimsuit. When you go out, are you worried about your hair being flat, your makeup getting oily? Your post dinner bloat that’s making you look like you’re in early pregnancy? Been there. These are things I’ve thought about, things I’ve heard many of my friends worry about. But you know when I find my friends, or women in general the most beautiful? When they’re just having fun. Laughing, dancing, carefree, and truly present in the moment. I know it’s easier said than done. Clearly I also catch myself when I slip. Anyway, that was a tangent (I feel like this entire blog is a tangent- I’m out of practice sorry lol). But like I said before, there’s so much we can’t control, and this is one thing we can. One thing that, I think makes a big impact. Shine from the inside out, and see how that positive energy attracts.
Anyway, back to my story.
I got there.
I spotted him in the middle of the grassy terrace, he was faced the other way. I think he was reading. I only saw the back of his head, but his hair was nice and flowy and he had on a loose butter yellow button down t-shirt. Very summery, and it looked great with his tan.
Me: Hi you!
Theo: Hii!! Nayomi!!
I liked how he always said my name with so much excitement.
Dating 101 Key Take Aways:
1) Positive energy attracts. When you’re feeling good, present in the moment, and radiating confidence and happiness, people notice. It’s not just about looks—it’s about the energy you give off.
2) Don’t c*ckblock yourself- Age, sandals with jeans, or other little things shouldn’t be automatic dealbreakers. Of course, preferences matter, but sometimes we get in our own way by focusing on the wrong things (including hyper fixating on your own insecurities). When someone is kind, engaging, and makes an effort, that’s what really counts.
