*Nolan, 45- The Gentle Gangster: Part 3
Pros:
Gentleman
BDE
Assertive
Thoughtful
Funny
Good vibe
Sweet
Committed to winning me over
Cons:
Not my type
Covered in tattoos and has lots of piercings (not really a con, just not my usual type)
Ever wonder what happened with Nolan? Did he really mean it when he said spending time with me was the cake, and anything more was just the cherry on top?
And more importantly- did he ever get the cherry?
Here’s the latest, and maybe the last, installment of my Nolan dates.
Nolan: I'm back in town. When can I see you?
Two things are always true when it comes to Nolan. 1) He was always gonna be direct, and 2) He was always on the move for work.
But the second he was back in town, I’d hear from him. He was consistent, persistent, and very romantic. And even if I saw it more as a friendship, it was hard not to appreciate that level of effort.
Me: Hiii! Welcome back! How was the trip?
Nolan: Long. Better now that I’m home. Let’s get dinner.
I always loved his assertiveness. He didn't beat around the bush and I also didn't have to think too hard. (Princess mode: Activated)
Me: I’d love to, but my friend is here visiting! Another time for sure
Without hesitation, he invited Julia too.
Nolan: Bring her. My treat. Just want to see you.
Honestly, dinner for me and my bestie? Hell yeah, why not. I got to explore whatever this thing was with Nolan, spend time with Julia, and eat good food- all wins.
I immediately asked Jewels if she’d be down for it. If she felt comfortable and wanted to go, great. If not, I wasn’t gonna leave her. But she was in.
We just had a littlee problem... As you guys know, that's my Celiac queen. And it's serious. Even a crumb of cross-contamination could ruin her night. She didn’t wanna be that person at dinner, running through a checklist of what’s safe and what’s not, and I didn’t want her stuck with a sad little side salad either.
Me: We’d love to! Thanks for inviting us both ❤️ But just a heads up, Julia’s a Celiac, so she has to be superrr careful with food.
Nolan: Got it. I’ll take care of it.
The hottest thing about Nolan was definitely his ability to handle things. He had this calm, but assertive demeanor, like there wasn’t a problem he couldn’t solve.
Me: You sure? I just don’t want her stressed about it or not able to eat.
Nolan: I swear. I’ll talk to the chef myself. We’ll make sure she’s good.
Me: You’re the best
Nolan: I know
That was typical Nolan humor. He’s always verryyy self-loving and jokes about it constantly. One time in the summer when we were planning to go to the lido together, he texted me:
Nolan: Just don’t be jealous if everyone is looking at me instead of you. Some people are just naturally irresistible.
Me: Yeahhhh, I'm sure that's what it is...
Mind you, Nolan is short, bald, and at the time, fat. (DON’T cancel me. That is literally how he self-identifies. And for the record, he’s VERY fit now.)
Honestly, I think he uses his humor as somewhat of a mask. He’s a gentle soul, really. And people are cruel. I mean, honestly, I had to check myself and my own judgments too. If I didn’t know him… I mean, he really looks... I can’t even say like a drug dealer, he looks like a drug lord. But he haaates drugs. Always has. Can’t stand them. Doesn’t drink alcohol either. He’s actually pretty straight-edge. It’s something I admire about him. But yeah, I feel like he cracks all the jokes possible before someone else does. Maybe it’s just built into his personality at this point. Or maybe, I’m totally wrong, cuz he also has a pretty convincing IDGAF attitude. Anyway, his jokes are always just jokes, and he has a way of warming your heart right after.
Nolan: No, I think if they’re looking at me, it’s definitely because they are wondering how I ended up next to the most beautiful woman here.
Me: I think they’re looking at you because your entire body is covered in tattoos 🤪
Since I was bringing Julia, Nolan asked if he could invite some of his friends too. Specifically, a few of the tattoo artists he sponsors. Of course, I was fine with it. You know how I think. The more the merrier. Also… it was his dinner. But it was sweet of him to run it by me anyway.
He wanted to make sure everyone was happy with where we went, so he asked me what I was in the mood for and checked on Julia’s preferences too. In the end, the grotto we went to last time just made sense- like, meat focused, less gluten options like pasta or pizza. So, we decided to go back.
It was a Wednesday when Nolan texted me. By Thursday night, we’d be out at dinner.
Nolan picked us up from my apartment. And because he’s Nolan, he had a little something for me.
Just as I got in the front seat, he handed me a little gift bag.
Nolan: I saw it and thought of you.
I gave him a ‘What is this?’ look.
Me: You didn’t have to.
Nolan: Open it.
Inside was a small, framed embroidered thing- it looked like something a grandma would knit. Delicate. Wholesome. Sentimental, even.
I tilted it slightly under the light, trying to make out the words stitched into the fabric.
“You have a nice ass.”
In fancy cursive. Gold frame. Just completely ridiculous.
lols…
“I had to!” he said, looking very pleased with himself. “It reminded me of you.”
I shook my head, still laughing.
Then he looked at Julia through the rearview mirror. “Julia... you know what they say? You know the way into a woman’s heart?”
I assumed he was about to say food. (For me, it’s food, vacations, and being nice to my friends.)
Nolan: Through her best friend.
Nolan: So tonight, Julia, you’re my best friend. I’m gonna make sure your every need is met. Whatever you want to eat, drink- anything- it’s yours.
I turned to Julia in the backseat and raised my eyebrows. Best friend telepathy.
When we arrived at the restaurant, Nolan was greeted by the owner like last time. The place was just as I remembered. Softly glowing with flickering candles, long wooden tables, no fuss decor. The smell of charred meat, garlic, and red wine clung to the air like an expensive perfume.
Nolan pulled out our chairs, always the gentleman, and, as usual, sat me right next to him. Nolan to my left. Julia to my right.
He asked us what we wanted to drink, but neither of us really wanted to choose for the table.
Nolan: Order what you want for yourselves, it’s okay. They can order when they come.
Julia and I got a bottle of white and just chatted with Nolan until his friends got there. About five minutes later… they showed up.
[Cue slow-mo camera]: Two fully tatted up guys, and by fully, I mean fully. Neck down. Actually, one was head down. He had a tattoo that crawled up his neck and onto the side of his face and head.
They were tall, fit, and very bad boy vibes. And right behind them, a crazy hot girl. A total baddie. Full sleeve on one arm and her body was tea.
They all looked hot and intimidating, and they literally seemed like they were moving in slow motion. Julia and I, who… are really NOT alternative at all (we’re like, kind of preppy, reformed clubbers), were in awe.
Julia was pinching me under the table.
I know… I know.
I think I’ve already said I’m not a tattoo person. It’s not something that I’m really into. But, for the first time in my life, I could see what people who are into tattoos see.
I saw the ~visionnn, guys.
I get it. It’s hot.
But despite looking intimidating and maybe like they were in a biker gang, they were SO nice. They went up to Nolan first, dapped him up, and gave him a hug. Nolan introduced us, and they hugged us, and introduced themselves- so warm and sweet. We all sat back down and started talking. Nolan told us about his friends and what they specialized in, in the tattoo world. They are literally the best at what they do. One specialized in fine lines (I think that’s what it’s called), and the other in hyper-realistic portraits.
And they clearly had a lot of admiration for Nolan too, which I thought was really nice. There was a lot of mutual respect there, and Nolan definitely gave them their well-deserved flowers. I love when people make others feel recognized and lift them up. Complimenting people, making them feel appreciated and seen. That translates to every kind of relationship. Roommates, friendships, romantic relationships. Isn’t that like one of the root causes of fights? Not feeling appreciated? So yeah, I liked seeing that dynamic.
Nolan: He did this…
Nolan got up, lifted up his shorts, and showed us his upper thigh. The most INSANE tattoo I’d ever seen. I truly have a newfound respect for tattoo artists. It was a portrait of Vito Corleone from The Godfather… (I think). It was very mafia boss-y. But it looked like an oil painting. Like a photograph. I don’t even know how you can do that on someone’s body and make it look so realistic, even with the natural contours of a leg. I couldn't wrap my head around it. Honestly, I've never seen anything like that.
After his show and tell, once again highlighting the talent of his friend, Nolan ordered for the table. He checked with the chef about what was gluten free and what wasn’t, then ordered us a cured meat platter to start, polenta (kind of like grits- not my favorite), and multiple platters of sausages, stews, and ribs. Oh, and these really nice roasted potatoes.
When the food came out, he walked Julia through everything that was totally safe for her to eat. The waiter mentioned that the potatoes had gluten because they were lightly coated in flour to make them crunchy. All it took was for Julia to say, "Aww, those look good," and Nolan leapt up.
Nolan: Let me go ask the chef if they can make a gluten-free version.
Julia: Noo, it’s fine, there’s so much other food, it’s fine, really
She really never wants to be an inconvenience. But like… we love potatoes.
Nolan: But you want them, right?
Julia: I mean, if it’s possible, but no worries if not.
Nolan: Like I said- anything for you!
And then he literally did a ballet pirouette, twirled around, smiled at us, and went to talk to the chef.
It was silly, playful, and cute. And I appreciated that he was trying his best not to make it seem like an inconvenience.
Julia leaned into me…
Julia: I know he’s not usually your type, but I love him.
Smart man.
Me: I know, he’s great.
I knew his end game.
He was playing the long game! And honestly? With how persistent, and genuinely sweet he was… I have to say, he was kinda growing on me.
A few minutes later, the waiter came out with gluten free potatoes for Julia.
Once she was fine and situated, Nolan turned to me.
Nolan: Would you like to come outside with me?
He smoked electronic cigarettes, and I knew he wanted some alone time with me. Even if I was cautiously dating him, just to see if there was anything beyond a friendship there for me, I still enjoyed all the time we spent together.
Outside, the night was cool, and the grotto, tucked away from the city, gave us a dark sky, a bright moon, and a great view of the stars.
Nolan: Are you having fun? And Julia? She’s okay?
Me: Yesss, we’re both having a great time, thank you so much. And thanks for making sure the food was okay for her.
Nolan: Of course. I know how much she means to you. It’s an opportunity for me to prove to you that I care about the things you care about.
Damn, he's really good.
And sometimes, I don’t even know what to say!
It’s so sweet, but also like, I was very clear from the beginning that I didn’t want to lead him on, and I didn’t know if I’d ever get to where he was at.
I gently rubbed his arm.
Me: Thank you, that’s very sweet. You are always very sweet.
Nolan: And you’re always very beautiful.
He said it as he put his cigarette in his mouth. He had a super Roman accent and a very distinct smell. Strong cologne, instantly recognizable.
I smiled, took a deep breath in, and focused on the view.
Nolan: I’m going to a tattoo convention in Rome. I want to invite you to come with me...
Me: What?
Nolan: Yeah, I’m driving down. Come! We'll have a great time. There’s this amazing café, I’ll take you there in the mornings. The best brioche you’ve ever had. Out of this world.
He grinned. "Trust me, I’m a fatty."
(His signature line.)
Me: Stop saying you’re fat! (laughing)
Me: Rome is nice… I know… but I don’t think it’s right for me to go with you. Isn’t there someone else you’d rather take?
I was kind of insinuating like, isn’t there someone who’d be happier to go… and also sleep with you?
Nolan: No, I’d rather take you.
Okay, let me be more clear.
Me: So you wanna bring me to Rome, and what… we go as friends and get croissants in the mornings?
Nolan: No, you go with me as my date and and stay with me. And you won’t regret it. (playfully elbowing me)
Me: Nolannnn…
Nolan: I’m joking. But you can come stay with me, and we don’t have to do anything. I would be honored to wake up next to you. It would be my pleasure, really.
Oh my God, I-
Did I already say he had a very formal way of speaking?
Anyway, I mean… no one can say he didn’t try.
Me: Maybe another time.
Nolan: Okay, I’d be lucky if one day I get the chance.
.........
I squeezed his hand twice and playfully smiled and winked.
Me: Should we go back inside?
Nolan: Yes, they probably brought out more food.
Nolan: Thank you for accompanying me, bella
(Bella means beautiful in Italian, but if you wanna think he was referring to me as Bella Hadid, I’m okay with that too.)
Nolan, ever the gentleman, held the door open as we stepped back inside. Maybe it was just me, but I felt like his friends and Julia were playing it cool, trying not to make it obvious that they were wondering what had happened. And honestly, nothing happened! We just talked.
We sat back down, and Nolan had already started serving me more food.
Julia gave me a ‘lil look. I ever so slightly nodded and smiled.
Once again- best friend telepathy. And if you're not a girl, let me spell it out for you:
Julia’s look: [Translation: You good? Did y’all kiss?]
My look: [Translation: All good. Nothing happened.]
You may be thinking- Wait a minute... how did your little nod mean you DIND'T kiss? Maybe it could've meant you DID kiss.
Obviously not.... that would have been me looking at her, widening my eyes for a quick second, and then looking away while pursing my lips together trying to stop the gossip from falling out of my mouth. A more literal translation of that would be: “OH my GOD, something happened. I'll tell you later b*tch.”
It’s incredible how women can communicate with no words at all.
We rejoined the conversation. Julia was telling them about her job and casually mentioned that she could get them Disneyland tickets (lol). Turns out, the really hot, tattooed woman was obsessed with Disney. Like, really, you cannot judge a book by its cover. She did look really serious. And then, she showed us her sleeve.
Upon close inspection… it was all Disney characters.
Her sleeve was Disney characters!! Wait how wholesome is that.
We kept talking, eating, and drinking. At one point, I asked one of the guys if his face tattoo hurt, and we all got into a full discussion about tattoo pain levels. “Like from 1 to period cramp to child birth. How painful are we talking?” I was obviously teasing the guys, bc obviously they've never experienced either of those things. It was just one of those unexpectedly fun nights where you connect with people you didn’t know before and everything just flows.
At times, when Nolan and I were laughing, we’d kind of lean in together. (Actually, laughter is definitely on the list of ways to my heart.) He’d sometimes rest his hand lightly on my knee while he laughed or told a story. Just little flirty touches, always within my comfort zone. And sometimes, he’d whisper in my ear to ask if I wanted anything else. That proximity, the way he’d get just a little closer... I don’t know. I felt like I was slowly warming up to it.
And then, at some point, I looked over at him.
The guy who had always put it all out there. Who gave me princess treatment. Who made sure I had everything I wanted. And for the first time... something…
shifted.
I won’t say I was all in. But I wasn’t against it, either.
You know that moment when you make eye contact with someone and feel a little zing.
Yeah… that.
Is this the first man to ever escape the friend zone?
After we finished eating, we ordered dessert. And oh my God, I had the most dangerouslyyy good lava cake.
Something about a hot, creamy, explosion, dripping out of a warm, moist cake…
Omg lol. I’m laughing while writing this.
Ya'll- I gotta chill...
Anyway, it was delicious. I always do my little happy dance in my seat when something tastes really good.
After I basically licked the plate clean, Nolan asked if I wanted to go back outside with him. These smokers really do need a cigarette after every meal.
I knew if he got the chance, he would kiss me. I knew.
But… I was in a good mood, so… maybe I was gonna be okay with it? I was full, relaxed, and happy. I don’t know. I had to see how I felt in the moment.
We went outside, and I kept him company while he smoked. We talked about my plans for the next few months. I think he wanted to plan the next date. Like I said, he travels a lot for work, and I had a few weekend trips planned, so I wasn’t always in town either. I appreciated that he wanted to lock in a date early.
So we were outside, talking... probably standing a bit closer than normal. It was dark out, just us under the moonlight.
What is it about moonlight that makes everything feel more romantic?? Is it the subconscious awareness that we’re just two specs of sand, standing on another spec of sand, floating in space? Sharing a fleeting moment together in one of infinite galaxies?
...It’s probably just the soft lighting.
I don’t know. I get weirdly hyper aware of my own existence if I think about the moon too much (as demonstrated above).
Anyway-
I feel like I saw him, maybe... in a new light.
Kinda like that John Mayer song:
But if you give me just one niiiight, you're gonna see me in a new liiiight
Yeah if you give me just one niiight, to meet you underneath the moonlight
Love that song.
Anyway, insert some invented dialogue here because honestly, I don’t remember everything we said. But I do remember this part:
[fast forward, fast forward. resume ⏩️⏩️▶️]
Nolan turned his head to me, a few inches from my face... There was a moment of tension... and then...
Nolan: I really want to kiss you
HMMM.………
I gave him a little nod- the green light he had been waiting for.
And let me tell you, he’s a passionate kisser.
Okay, well, we can’t go from 0 to 100 here, so… that was it.
Me: Okay, we should go, they're probably waiting for us.
He offered me his arm to walk me back in, and I giggled and took it.
I mean he really is a Disney prince with a Disney villain exterior.
When we got back inside, Julia's eyes darted towards me. My eye's widened and I pursed my lips. She raised her eyebrows in surprise. We would do a full debrief later that night.
Anyway, Nolan asked for the check, and while we waited, our waiter showed us his rap mixtape (lol) and poured us some digestifs (post dinner drinks). I opted out, but Julia was having a great time (she can also just like drink way more than me and still function.) The waiter was hardcore flirting with her, and at one point, he jokingly asked for a kiss.
We were all in a funny mood and started chanting: Kiss! Kiss! Kiss!
And to my surprise, Julia actually gave him a peck!
Everyone is in a kissing mood tonight.
Afterwards, Nolan asked if we wanted to go home or go see a nice view before he dropped us off.
Me and Julia, in unison: View.
We would almost never pass up the opportunity to see a good view.
I have no idea where he took us, but we drove up a mountain to a lookout spot. The lake was stunning (APU- as per ~usuAL), and oh! Julia and I may or may not have taken our wine glasses from dinner. Nolan said he’d return them to the owner, so we walked out of the restaurant Rihanna style.
We sipped our wine, it was a clear night and we just took in this beautiful place overlooking the lake that he brought us to.
Nolan came behind me and wrapped his arms around me.
I wasn’t trying to be overly romantic in that moment. Julia was literally right next to us, but… carpe diem, or whatever.
Me: Well, this would make a funny blog.
Nolan: What blog?
Wait-
Me: You didn’t know about my blog?? You follow me. You don’t see my stories?
Nolan: I do. I saw something, but I didn’t know what it was! Tell me more.
So, I told him. About how I started writing about my dates, how people liked it, how it was funny but also kind of educational- LOL, why am I explaining this to you, you guys get it.
Me: But don’t worry, I won’t write about you!
When I started this, I assumed most people wouldn’t want to be written about. But boyyyy was I wrong. The amount of guys who actually want to be written about, or even ask me out by saying, “So… can I be the next blog entry?” is insane.
Everyone wants their 5 minutes of fame.
Is this the power trip Hollywood exec’s have??
Nolan: Why not?
Me: Uhhh… I assumed you wouldn’t want me to?
Nolan: No, you must!!
Me: Really?
Nolan: Yes, of course.
Me: Well, you know if I tell the story, there’s no holding back. It’s the truth.
Nolan: I wouldn’t expect any less.
Me: Okay… if you’re sure… I don’t wanna make it weird.
Quick sidebar- because people always ask me this. Morally speaking.
Do I tell the guys I’m dating about the blog?
No. Not unless we’ve gone on a few dates and I feel like they should know.
That said, if I care about someone or we’ve become friends, I always give them the courtesy of a first read. I ask their permission before posting. I give them the chance to ask for changes if they want. I really do try to be as respectful as possible.
But, no one’s ever taken me up on that offer.
Usually, I get something like:
“It’s your story.”
“It’s fine, I trust you.”
“You’re talented, I’m not gonna cramp your style.”
And honestly? I think that’s pretty cool. I’ve been lucky to share moments with some genuinely cool, confident, kind, guys who let me tell my story, my way.
So one day, when Oprah asks me: “Were you SILENT, or were you SILENCED?”
I’ll say: “NEITHER, I spoke my truth!”
Alright, back to Nolan. Let’s see how he really felt.
…
Nolan: YES! You have to let everyone know I got this far! I didn’t even think I’d get a date. This is a success for me!
Me: WHAAT!??
Nolan: Yeahhh, you think I expected to get a kiss??
(shaking his head)
Nolan: Maybe I’ll inspire others. Anything is possible.
Honestly, he was fully leaning into the bit- and we were dyinggg laughing.
He was cute, fun, sweet. And he was so thrilled to have sealed the deal with a kiss.
Me: Okayy, I'll write it.
Anyway, that was our last date.
It didn’t go far romantically, but he’s definitely still a special person in my life.
Usually, when these kinds of connections don’t turn into something romantic, they end with bitterness or fizzle into nothing. But with Nolan, that was never the case. I made my feelings clear from the beginning - I always saw it more as a friendship. I was honest about where I stood, and he was determined to try, but he never had any expectations. I think because of that, it was easy to stay friends.
And not just surface-level friends. Like, actually show-up-for-each-other friends.
When I had my knee surgery, I was in terrible pain. I couldn’t walk- my parents were literally pushing me around in a wheelchair. I’ve said this in another blog, but Nolan literally refused to let us taxi to the hospital.
Nolan: Are you crazy? That’s what you have friends for.
And when my hospital stay ended up being longer than expected, he still showed up.
He visited me- twice. Once, coming straight from the airport after a business trip, getting there just 15 minutes before visiting hours ended. Another time, he brought cannolis, for me and my parents.
And when I was finally discharged, he was the one who picked me up and drove us home.
Sometimes you wonder if guys pull out all the stops just because they want something in return. But with Nolan, it wasn’t about that. It’s just who he is. Thoughtful. Reliable. A genuinely good person. And he never made a big deal about it.
Maybe, yes, he did like me. He made that clear.
But once we were just friends, he showed up as a friend.
I’ll never take that for granted.
And when I finally met someone and it got serious, I let him know.
Nolan: I’m happy for you. You deserve it. And this guy must be pretty special, because you picked him over me 😜
He always knew how to lift me up.
Me: Thank you… I really appreciate it. Honestly, I knew you’d be happy for me but I was a bit worried to disappoint you
Nolan: Relax Nayomi, I love you- but I’m not IN love with you 😉
LOL. Okay then.
He really took the L with grace, cracked a joke, and stayed my friend.
But also, you don’t have to stay friends with someone you dated. In most cases, you won’t.
But you don’t have to be a hater either.
I was genuinely impressed with how he handled it. With grace, with humor, and without making it weird.
Honestly, I couldn’t have asked for a better outcome.
And for him?
I guess he got the cake
… and the cherry on top.
Dating 101 Key Take Aways:
1) Give people their flowers. Don’t be stingy with your compliments. Make people feel seen and appreciated. Lift up the people around you-whether it’s friends, family, someone you’re getting to know, and especially someone you’re in a relationship with.
2) Don’t judge a book by its cover. You’ll write off a lot of people before ever having the chance to get to know them. And not just in dating-in life. We’re quick to make snap judgments, but people will surprise you. Sometimes, the guy who looks like a real-life gangster is actually the most gentle person in the room.
3) If you’re gonna shoot your shot, shoot it. But if you miss, take the L with grace. Nolan put himself out there, played a great game, didn’t get the W, and still stayed a real one. That’s confidence. That’s cool. That’s how you do it. I’m not saying you have to stay friends with people you dated-but you don’t have to be a hater either.
