#067: four first dates

Happy 2025, y'all! Why does this month feel like a whole year in itself? Can January be over already? Because I'm tired.

These are weird times and I don't feel like talking about any of it, so instead I decided that it's the perfect time to talk about jumping head first back into the streets. It's been fun, to say the least…

the story
I was back, and I was ready. After taking months off from dating, I’d finally found it in me to put a little outfit together, flip on a pre-date playlist, and get myself in a good ass mood so I could flirt again with cute men. This time felt really different. There was something in me that felt calm, assured, capable of anything that came my way. A part of me had shifted…thank gawd. For awhile there I was worried about how long I was able to go without even desiring to go on a date. 

Before my therapist went on maternity leave (hey girl, you still owe me pictures of the baby!!!) we talked about dating and what I truly desired in a partner. For the first time, I got really clear on what I needed. What followed soon after was four first dates. So without further ado, let’s go on ahead and unpack my re-entry into the streets. Here we g0o0o0o!!

My very first date was with another yoga teacher, because of course it was. We went mini-golfing on a Sunday afternoon and bonded over yogic philosophy, being terrible at mini-golf, and how we desired to live our lives outside of climbing the corporate ladder. He was such a sweetie. In true Astro girlie fashion, I tried to guess his sign and found out that man was a Cancer Sun, Pisces Moon, Leo Rising….woof. But what I liked was the fact that he wasn’t one of those guys who rolled his eyes and had something ridiculous to say about women and astrology. I had a lot of fun and the conversation was great, though my only concern was how deeply it went. It wasn’t a bad thing, but mans seemed like he wanted to go for deeper, more vulnerable topics right off the bat and I’m a pretty lighthearted person when you first meet me, especially when it comes to first dates. My goal for the next date was to understand if he could just enjoy himself and have fun, without plunging into more serious topics.

I called my Uber and texted Imani as I headed home, telling her it was actually a great time?! On a whim, I rerouted my Uber to Dumbo House to meet up, stuff truffle fries in my mouth and spill the tea. The funny part was, I wasn’t necessarily excited about the date because of who he was or some crazy spark between us. I was excited because I felt like I’d successfully picked someone who aligned with my values. I didn’t get the ick from a person whose interests are more in line with mine and less with the soul-less corporate guys or athletes I’d been prone to picking. This guy meditated, did yoga every morning, would walk up to five miles a day and was more on the goofy side. Honestly, it was a fucking WIN. We breaking patterns up in here baby, but anyway.

On our way out of Dumbo House and fresh off my post-date high, I orchestrated my own little meet-cute. Now, if you ever ask Imani, she’ll tell you that my ability to pull men at Dumbo House is pretty impeccable and often jokes that her membership must really be for me. The gag is, I can pull them but I usually end up getting the ick pretty quickly. It’s genuinely not my fault they’re all full of themselves!!

I’d spotted a cute guy behind us as we left and overheard his conversation with the receptionist.

“Leaving already?”

“Yeah, I forgot my headphones,” he’d replied in a cute British accent.

“Forgetting your headphones is crazy,” I playfully butted into the conversation and looked over my shoulder at him.

After a little chitchat outside of Dumbo House with Imani and myself, we all exchanged IGs and went on our way. He’ll come back up a little later…

One thing about me, I love an activity date. I feel much more comfortable if I have something to do besides stare at a man across from me who I don’t know and make conversation for two hours. Let’s bond over something interesting and fun, pls!! For the record, my Venus is in Gemini, but anyway. My next first date was axe throwing and I was better at it than he was, if I do say so myself. This guy was a little awkward at first and I, truthfully, had a great time watching him struggle to throw an axe. We had dinner afterward, then dessert, where we both got the things I wanted so that I could try each of them.

One thing I immediately realized about him was how considerate he was. For example, he told me he was really good at making cocktails. I let him know that I was actually a mocktail girly. Instead of making it weird or asking me why, he simply volunteered a picture of his favorite mocktail he’d made and said he had me covered. The conversation on the date was fun and lighthearted and by the end of the date I felt neutral. He was sweet too, so I’d decided to give him a second date.

The next week I told him I was really tired, so we planned to do a lowkey dinner. He randomly told me he’d almost gotten himself tickets to the Usher concert, but had decided to sit down somewhere instead.

“Really?” I’d replied, “even I would get it together to go see Usher.”

“So…if I happened to get us Usher tickets for tomorrow night, would you be able to get it together?” he said.

“Um, YES?”

The next night I found myself with incredible seats at the Usher concert. I had an amazing time and felt so good. I barely knew this man, but that certainly would not stop me from revealing my true self and screaming Usher lyrics at the top of my lungs. I loved the confidence that came with giving myself a little beat, slicking my hair back, putting a sexy outfit on, and knowing that man had to look but not touch, okay?! Shoutout to him too, it takes a lot of strength to watch the girl you’re dating scream and fangirl over Usher for almost three hours.

Naturally, I posted myself on my IG stories screaming Usher lyrics the next day. Seeing my little DM notification pop-up, I giggled to myself as I realized who it was: Mr. Dumbo House III himself. We exchanged a few flirty DMs, swapped numbers, and next thing I knew, I was booked for my third first date.

We met at a bar in our neighborhood after I’d casually let him know beforehand that I’d be drinking mocktails. I have mixed feelings about bars as first dates, but I’m realizing that my aversion to them was adopted from an opinion that isn’t mine. I’m down for a nice bar that allows for conversation without tying people to a full dinner, as long as there’s no expectation that a lot of alcohol will be consumed. Anyway. The conversation never got old and the chemistry was definitely there. Veryyyy flirty energy. Now, when this happens I’ve learned to stay alert. Men suck at controlling themselves, so if they sense the chemistry it makes it even harder for them to act right.

As the date went on, he kept getting closer to me, eventually breaking the touch barrier way too early. By the end of the night we were sat next to each other in a cozy bar, legs touching, with him gently grabbing my hand. Now, some girls don’t mind stuff like this. I do, because sir I do not know you!! I made a mental note of the orange-red flag and wrapped up the date. As we said goodbye, we kissed in a pretty adorable way. We laughed as he playfully told me to “compose myself!” What happened next, however, sealed that man’s fate quicker than I have ever seen it done.

He hugged me, his hands floating dangerously close to my behind. The next thing I knew, that man was grabbing my ass. I kid you not. This boy I’d known for a total of THREE HOURS had the audacity to touch my booty. In the moment I laughed but also told him he absolutely could not do that. Naturally, I ended things the next day when he followed up. That was wild, but makes for a good story.

There was another first date, but it was honestly so boring I don’t have the energy to write about it. The man was way too serious. How does one not even laugh once on a first date? Thankfully, he also realized it wasn’t a match and I did not have to break it to him myself.

So those were my four first dates y’all, and I wouldn’t take back any of them. Not even the booty grab. I didn’t like every person and it’s not like they all went amazing, but they did show me how far I’d come and how much I’d grown since my last relationship. That made everything worth it.

the lesson

Come with open energy. I’ve gotten the feedback a few times now that my energy feels really open and welcoming. I love that compliment, especially because I truly do feel that way. People sense energy, no matter how well you think you’re hiding it. What you feel internally is often the same vibe you’re giving out, so if there are certain ways of thinking from your past that you’re still hanging onto, you may want to take a beat and examine them. Men can sense bitterness and desperation, and it ain’t cute to the ones who did nothing wrong to you in the first place.

Pause, think, and do something differently. In the past few months I’ve learned that my default is to immediately find a solution or power through whenever there’s a bit of tension or discomfort. I rarely pause and give myself space for the initial emotions to settle before I make a decision on something. For example, the moment I got my ass grabbed my immediate reaction was laughter, shock and de-escalation. He probably thought everything was fine. It was hard for me to compute in the moment that the guy who I’d had the best time with out of all my first dates was violating my boundaries in the most ridiculous way possible. By the next morning, I’d resolved that when he followed up I’d be super clear and vocalize exactly why he’d messed things up. A previous version of me probably would’ve still broken it off but lied about why to avoid addressing his bad behavior. Instead, I let him know that I had a really good time but ultimately he made me really uncomfortable by doing that. It felt really good to speak up and say how I felt instead of avoid the conflict — now hopefully he won’t do that to anyone else.

Dating is a masterclass in boundaries. You are your best advocate, don’t leave that work to anyone else. Know what you need and what makes you feel comfortable. For example, I don’t like dates that start past 8pm and prefer that they start way earlier. I do not mind a date in the middle of the afternoon because I like to be in the bed at 9:30pm. Even starting a date at 8 is throwing my sleep schedule off, but I’m learning to live a little since the majority of the world doesn’t operate this way. I also feel like the later the date starts, the more men think they have room to make a move on you. If at any point someone asks me for a later date time, I politely push back. If they have a poor reaction to it, they’re simply not my man. Boundaries are something that keep you feeling mentally safe and secure. If he can’t respect them, then he probably won’t be the person who provides much peace in your life.

the light

Dating has actually been really fun, but that’s because I create the conditions for it to be that way. Not every date is a W, however, I feel a lot more confident in my ability to choose what’s right for me. Not every date is a W, but because I’m actively breaking my own patterns and making different choices, I know that I’m closer than I’ve ever been to finding the right person. I’m not going to get it right every time, but I have confidence that I even if I do make mistakes, it means I’m supposed to learn something new. There’s a certain level of security I feel, maybe because I spent the majority of last year super single, that helps me not be so attached to the outcome. If the worst case scenario is me being single for a little longer while I grow more and get better at this whole dating thing, I think I’ll be aight.

Dating can bring up a lot of emotions, so let me be the one to remind you of a few things:

You can always start over and choose to be better, one experience doesn’t have to define all of them. 

Sometimes it’s you who needs to change and that takes time, be patient with yourself. 

There are still good people out there.

my matcha moment 🍵

Have y'all heard of the Hatch alarm? I am obsessed. I've been sleeping without my phone in my room for around six months now, which has made a huge difference in my sleep. This little alarm has taken it to the next level though. Essentially, you can create your own little wind down and sleep routines that help you fall asleep and do the same for the morning. I've found that the light pairings with soothing sounds help my mind actually feel like it's bedtime. Because I wake up before the sun comes up, the “sunrise” that starts 30 minutes before my alarm goes off helps my body to wake up. 

Sleep is so important for the mind and body, which means I don't mind splurging on something like this. They are expensive and definitely a luxury, but for anyone who has an HSA or FSA, you can buy it through TrueMed.