Dating Diaries S2 E1: Dating the Bachelorette Style

Bella's Journey
4 min readJan 17, 2024

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How many men are TOO many to date?

Photo by Nong on Unsplash

It’s time for a new season of my life — the single and ready to mingle dating-app style!

I have so much to catch you guys up on — some juicy things, and even kind of scandalous things…

Let’s get into it!

My ex and I broke up in October, and so I found myself single. I got asked out the next week, went on the date, and ultimately decided that guy wasn’t it either. It didn’t take long for me to quickly download 2 dating apps: Match and Hinge.

Now, I will tell you…I saw a HUGE difference between those two apps and maybe I’ll write a completely separate post on that.

By the end of 2023, I had gone out with 8 different men and by today (mid January), I now have 4 men that I’ve been consistently talking to, which makes me feel like I’m participating in my own version of the Bachelorette (which by the way is SUPER stressful).

Let me introduce you to our top 4 contenders (names have been changed):

  1. Neuro Nick — a nerdy and cute, but very sexually open neurologist who works for the military. This is my top favorite, but I still have my reservations before I attempt to have an exclusivity talk with him.
  2. Gentlemanly Gary — an old-fashioned conservative but fun man I went indoor mini golfing with. He’s currently getting into religion, so I’m not sure if that might not be a problem down the road.
  3. Nursing Ned — just got out of nursing school and also has a special needs sister. Unsure if we may not be TOO similar to work long-term.
  4. Italian Ian — such a hottie, and we have all the same values, but unfortunately his family is going through a major health crisis so our current date plans are on hold until he gets back.

I’ve lost count of how many times I’ve seen Neuro Nick. Partially, because on some days, I’ve seen him twice.

Here’s the rundown on my favorite contender:

He’s someone who is very family oriented which I absolutely love. He makes me feel comfortable in the way that I don’t feel pressured to do anything I don’t want to, and he encourages me to actively ask for what I want (which is something I’m not the best at). He also makes pretty good money and is putting in a lot of effort in pursuing me.

Now what made us have a rocky start is that the first time we were scheduled to FT, he actually ended up missing it. The time we met up for a quick coffee, I for sure thought it would never progress to a second date because it felt more friend-y than romantic.

And to be honest…there are still times when it feels more like friends than dating BUT….

the sex….is out of this world….

He was very open about that he wasn’t exclusive in the beginning. He told me he was seeing and sleeping with other people. Or at least told me that that’s how he usually goes about dating until exclusivity is discussed. At first that bothered me, because I didn’t want to be one of many but then again I was meeting a bunch of different men as well…the only difference was I wasn’t getting physically involved with multiple men.

When we slept together first, I was hesitant, and I was ready to call it mentally quits after. Just because I knew that whether our sexual chemistry was good or not was going to be important enough to him to decide whether it was worth pursuing a relationship — a mindset I’m not a fan of. So I prepared myself for the worst — terrible sex or sex that felt awkward and he’d be like sayonara!

I didn’t have a ton of experience with 3 past sexual partners at age 29 so I wasn’t confident in my “performance” abilities. (Don’t even get me started on blowjobs!)

But….it was the best sex I had ever had. And he agreed.

Since then, he has called me nearly every day, texts me from morning to night, has planned various trips for us to take together, and even flew for the day to visit me while he finishes up his rotation somewhere else. He also gave me the apartment key so I could cat sit for him while he is gone (which feels like a big step considering that those cats are like children to him).

Yesterday, he told me I was the only person he was seeing or sleeping with. While I couldn’t exactly say I wasn’t seeing other people, I COULD say that I wasn’t sleeping with anyone else. And then we returned to napping in each other’s arms (sounds disgustingly romantic, right?).

Anyways, in an effort to not get too hung up on him and the fact that we weren’t exclusive yet, I continued to see the other 3 men. I’m going out on second dates with Gentlemanly Gary and Nursing Ned this week and just got off a FT date with Italian Ian.

I won’t be seeing Neuro Nick for another 2 weeks unless something changes last minute, so until then I will keep focusing on myself and seeing if any of those other 3 can be taken out of the roster or rotation.

How would you handle dating multiple men? How many men are TOO much?

Toodles,

Bella

P.S. Next post I’ll tell you guys about my unexpected run-in with my ex, Finance Frank.

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Bella's Journey

A scorpio in every single way - a lover of deep intimate conversations, intense connections, and loyal. Buy me a coffee :): https://www.buymeacoffee.com/bella94