Press play on the Sex and the City intro—because I’m fully in my Carrie Bradshaw era.
I went on five dates in one week after being out of the dating world for years, having been in a long-term relationship. Was having five dates overwhelming? Absolutely. Did I do it partly for material to write about dating in 2026? Of course.
Those five dates spanned three men, each with completely different personalities, careers, styles, and relationship histories. Each taught me something new—not just about them, but also about myself and how I want to show up moving forward. Part of me feels a little conflicted about using my experiences with these men as research material. But I approached each date with an open mind and an open heart. If Carrie could write about her dating life, why couldn’t I?
Plus, I live in a house of four single women, so it feels like a rite of passage to live out our very own pilot episode.
First Date: 26 years old, Mechanical Engineer
My first date was with someone who recognized me from college. I didn’t particularly remember him, but the familiarity of a shared past felt like an easy icebreaker. He picked me up and drove us to a ’70s-themed bar, where we both dressed in retro attire and ordered fruity cocktails from the inspired menu. We sat in a booth, watching a lively group of seniors dance to vintage hits from the DJ.
The music was a little too loud, and I felt nervous figuring out how to converse with someone who knew almost nothing about me, especially since I was accustomed to the deep knowing that comes from a long-term relationship. He dropped me off, kissed the back of my hand, and later texted he’d love to see me again.
Our second date was later in the week, on a day I was feeling particularly anxious. Instead of judging or distancing himself from me, he showed up at my house with calming lavender tea, a small potted Christmas tree, and a fresh bottle of Ashwagandha (a natural anxiety supplement). We ended up having a great time, visiting a museum and getting to know each other in a quieter setting. On the drive home, he told me he has a tendency to move quickly in relationships he’s interested in and was wondering how I felt about him. I sat in the car, fighting the urge to be overly agreeable.
What was I looking for? Someone to casually hang out with? Companionship? Monogamy? I realized I wasn’t sure.
Second Date: 28 years old, Medical Technology Salesman
My second date was enthusiastic, driven, and open about his past and family in a way that allowed us to connect emotionally. We met at a bar and ordered a couple of drinks. Sitting on barstools, our knees nudged under the wooden top with nervous energy. Our conversation wove through family history, spirituality, mental health, therapy, travel, and the realization that we had both been in long-term relationships before. We had a lot in common on paper, but I struggled to figure out how I felt.
Our second date happened later that week. He picked me up and drove us downtown to see the Portland Christmas tree. He greeted me outside and opened the car door with a smile. As we crossed the street, he offered me his arm while we navigated through the crowds. It was thoughtful and unexpected.
We went to a bar afterward for a drink, where he insisted I was flirting with him. I sat there confused, feeling like I was simply carrying the conversation and showing genuine interest in his story. Where was the disconnect between what I felt and what he perceived? He held my hand as we walked back to the car, a bit giddy.
I went in assuming the worst—2025 dating horror stories are everywhere—but he planned the date, picked me up, treated me with respect, and spent the evening communicating how interesting he found me. But, did I find him interesting?
Third Date: 35 years old, Bartender
This date was very much a do-it-for-the-plot wildcard. A full decade older than me felt like a stretch, but… why not? We met at a bar and spent most of the night talking about music. Our lives seemed to exist in completely different chapters, so finding common ground—even briefly—was a relief.
He drove us to a comedy show, where we squeezed into a tiny table at the back of the room. I noticed he struggled to make eye contact and didn’t ask many questions about me. I assumed it was nerves and gave him the benefit of the doubt—at least he seemed genuinely happy to be there.
He was lighthearted and fun. I realized he loves music just as much as I do when we both sang out to I Wanna Rock by Twisted Sister on the drive home. He invited me to join his friends afterward, but it was already late. I was intentional about listening to myself about whether I wanted to continue the date that night or not.
Am I the emotionally unavailable one?
All three men asked to see me again—with an enthusiasm that felt both flattering and, at times, a little overwhelming. In fact, dates one and two expressed wanting to be in a committed relationship with me. Being not even four months out of an almost decade-long relationship has left me feeling emotionally cautious, if not slightly unavailable. Still, I keep reminding myself: dating can be fun. Dating can be casual. Spending a few hours enjoying someone’s company doesn’t have to mean anything more than that.
I set out to write a cheeky piece about dating and the dance of flirtation, but instead I walked away with more questions than answers. Having just dipped my toe back into dating, I realized I didn’t really know what I was doing. But does anyone? Connection can strike unexpectedly, yet dating with the explicit goal of finding it narrows your focus to whatever is unfolding in that single moment, right there across the table.
What surprised me most was these men’s desire for monogamy and a committed relationship. I went in expecting the opposite—something casual—like the dynamic so many women mock online, the archetype of the 32-year-old man who “isn’t ready for a relationship.”
Maybe I just happened to stumble upon a handful of men who happened to want relationships, or maybe I’m just quite the catch, which seemed the case watching them fight for my time all week. A little ego boost after a breakup never hurt…
As the week went on, I realized I hadn’t actually asked myself what my own intention with dating was. And once I did, the answer was clear: I wasn’t looking for a committed relationship. Still finding my footing after a nine-year partnership, the last thing I wanted was someone who required my full attention while I was finally learning how to give that attention back to myself.
Which made me wonder—was I the emotionally unavailable one? Had I become the man I was so sure I was going to meet?
If I had to give any advice based on my experience this past week, it would be to map out your intentions. Being able to communicate them clearly can prevent gray areas, avoid leading someone on, protect your boundaries, and save everyone the mental energy of overanalyzing what’s happening. This brings me to my next point: honest communication.
Breaking the first-date script
I’ll give myself a pat on the back here, because I didn’t realize I was already doing this until every date explicitly thanked me for it. Toward the end of each date, I’d ask, “How do you think this went? What’s on your mind?” Most reacted with surprise, then curiosity, telling me it felt unusual—but refreshing. I was the one who felt shocked, since this is how I try to approach all my relationships, when I can.
Now, I’ll admit—maybe this put them on the spot. Would someone really tell me to my face that they didn’t enjoy spending time with me? I know I probably wouldn’t. But even if certain feelings remained unspoken, those questions opened the door to more honest conversations: past dating experiences that left us confused, preferred communication styles, and how we show care to people we love.
I realized that these questions—awkward at first—built trust quickly and allowed both of us to relax. They stripped away the formality of early dates and replaced it with something far more grounding. We embraced the simple human experience of getting to know someone and feeling nervous about it. How ordinarily magical.
The weight of a kiss
Since I wanted this piece to be a bit cheeky, I have to talk about the hardest part to navigate: the end-of-night kiss.
By the end of date two—and date one, in the case of the 35-year-old—I realized there was always a kiss looming. This isn’t new; men and women have been doing this dance forever. Still, it raised a question for me: is the kiss an accepted expectation?
At the end of my second date with the engineer, he leaned over the center console and kissed me, his hand on my cheek. With the salesman, it happened on the steps leading up to my front porch. The bartender? In his truck. I could have gone without all three—though I’ll admit, the possibility of feeling a spark is intriguing. What unsettled me was realizing I never even considered turning them away. That would be rude… right?
That’s when it hit me how deeply the patriarchy has its teeth in: I was prioritizing their desire over my own boundaries. But to be fair, I hadn’t defined those boundaries—not even to myself. So with each kiss, I participated, if only out of personal ambiguity.
I asked my roommates about it, and they all agreed: there’s almost always that moment at the end of a date when the kiss enters the room. Sometimes they’d do it just to get it over with; sometimes they decline when there’s clearly no chemistry. While a kiss can feel fleeting—an easy bridge into physical contact—the implication carries more weight. It’s consent to another person’s touch, to the idea of future touch, even to attraction itself.
I began to wonder if accepting the kiss can get you into more trouble than refusing it. Walking away from my week of dating, I made a vow to never kiss again unless I truly want to. That’s how it’s supposed to be, of course.
Five dates, zero regrets, one revelation
After that whirlwind of a week, I realized that five dates in seven days was far too many. It felt like a part-time job—coordinating plans, getting ready, being on, then decompressing afterward. The texting, the calling, the kissing, the wanting and unwanting. I was fully absorbed in the worlds of these men, slowly disconnecting from my own simply because there was no time left.
With some distance, it became clear that what I’m most drawn to right now is deep, uninterrupted time with myself. I like taking myself on dates, investing in my friendships, and creating space to just be.
It sounds like a cheesy ending—the girl chooses herself instead of chasing a man, finding strength and confidence through independence. But honestly? Hell yeah. This isn’t a rom-com punchline; it’s real life. If anything, this chaotic week reminded me just how sacred my time and body are—and what a profound reminder that is.
I don’t have many answers, but I do know this: staying connected to yourself and your intentions, communicating honestly, and giving yourself permission to kiss—or not kiss—feels like the bare-minimum roadmap for dating.
Carrie Bradshaw makes it look easy. Then again, she is a dating icon. Maybe one day I’ll walk in her shoes—or her Manolos, if I’m lucky.
