Let’s talk about Fitness Chick. Specifically, how she ended up being the only woman I’m seeing now, the advantages and disadvantages, and how this mixes with my bachelor lifestyle.
I mentioned in my previous newsletter that she is the only woman I’m currently seeing. The story from our first date until now is surprisingly long, as in two years. Our first date was in July of 2022; I had reentered the dating market in January of that year. I was immediately attracted to her - blonde, great shape, easy smile, and smart. I constantly went on first and second dates that summer and she was not a stand-out. She was competing with the Squirter, amongst others. The Squirter insisted we have sex at her home because her bedding was designed for her “gift.” She was not exaggerating; she was like a garden hose. I like it when I make a woman squirt, but she was in another league, and we were soaked afterward. Once warmed up, she gushed from simply being kissed hard and slightly restrained. I digress, but that was a fun walk down memory lane!
I told Fitness Chick I was too busy to date and moved on. However, she did not and reached back out in October. From then on, she became part of my rotation, and I saw her a couple of times a month, enjoying her company and having great sex.
By the summer of 2023, I was increasingly uncomfortable with her feelings toward me; she was becoming quite attached. I brought it up several times, and she denied it; my reaction was to see her less and keep her at arm’s length. Truthfully, I didn’t trust her emotionally; she was out of touch with so many true feelings and caught up in the vicious cycle of perfectionism that I was in as far as I was willing to be. And me being who I am, I felt somewhat responsible for her feelings towards me.
And then crazy happened. And I stopped seeing everyone else. When I told Fitness Chick I was ending things because I was seeing someone else, I could tell she took it hard. And then I ran into her two weeks later in town and thought she was going to cry. That was October 2023.
Flash forward to the beginning of this year: She reaches out unsolicited and wishes me a happy birthday. One thing led to another, and we started seeing each other again; she hadn’t forgotten me, and I couldn’t forget the sex. But it felt different this time; she was (and still is) in a much better place than last year. She asked me to be her date at a wedding that her ex-husband was also attending; I went and got to play the part of her protector; you can imagine how that made her feel.
I was seeing another woman when things rekindled with Fitness Chick. She was not nearly in as good a shape physically or emotionally. It’s funny/not funny what you learn about someone when you sleep with them—like all the pharmaceuticals they take to help them get through the day.
I’ve concluded that the two most important pieces of information about someone you can learn during midlife dating are their credit score and their current prescriptions. Woman number 2 was wealthy beyond anyone I’d ever dated before, and the number of meds she was on was shocking. I had my hands full with work and managing my dad’s health, and I needed to cut back on dating, so it was easy to decide which woman would be the one I would continue to see.
So here I am, dating one woman who is entirely in love with me even though I do not reciprocate those feelings; I like her a lot, and she adds to my life without asking for much (a huge factor in why she’s still around - I’m sure she’s figured that out). I’m not freaked out, and I’m not feeling stifled or smothered. Nothing has changed in my life other than we’ve met some of each other’s family and friends. We’ve agreed there is no commitment between us, although I’m not sure we share the same definition. And we’ve agreed there is no vision of a future; we’re taking it as it comes.
My relationship history can be characterized by co-dependency. Previously, I went all in and found personal meaning through being in a relationship. I tended to lose myself in the other person. I’ve mentioned that dating multiple women was an antidote against repeating this behavior. Said another way, I didn’t trust myself to date one woman. However, I am finding that I can maintain my differentiation, which significantly boosts my self-esteem. For the moment, a form of monogamy, which I’ve heard referred to as monogamish, is working for me.
I’ve let go of feeling responsible for how a woman feels about me. I am simply being myself and letting her do her thing. We have discussed this, and she knows she’s the captain of her emotional ship.
There are clear advantages for me being monogamish. First, it’s cheaper; endless first and second dates add up quickly. Furthermore, we’re now at the stage where she’s simply happy to come over, I make us dinner, and we have sex. I like to do fun things and plan outings, but now I don’t feel I always need to do that. Secondly, it takes much less effort than spinning plates. It is an effort to track what I’ve done with whom, their kids, their history, their likes and dislikes, and even bedroom preferences. I happily did it for two-plus years, and I fully admit I’m enjoying not doing any of that now. Her adoration and loyalty have shifted to the next level, and I almost feel guilty for enjoying it. She is overflowing with honeymoon-phase emotions, and I am reaping the benefits of this. I’m not playing games with her emotions; she knows she is respected, appreciated, and safe with me and has told me so.
There are clear disadvantages as well. There is no way she will not be hurt when things come to an end; I can’t do anything about that other than not let it hold me back when the time comes unless she beats me to it. Even though she’s very low maintenance, there are still things that feel more monogamy than monogamish, like listening to her family and friend drama (I'm not too fond of drama). Part of me misses the chase of meeting new women and seeing where things go; the thrill of the hunt is real for me. I am exerting some effort to remain detached and not fall in love because that is my relationship habit pattern.; it’s worth it, but it’s a thing. What helps significantly with this is reminding myself that I’m in love with the life I’ve created far more than I could love a woman. And truthfully, there’s a slight fear of letting another woman in deep and then getting hurt once again.
Simultaneously, an advantage and a disadvantage is the effort of maintaining frame. The advantage is that I can practice not falling into her frame, and the disadvantage is that I find it easier to spin plates than maintain a frame with one woman. I’ve learned a valuable lesson about frame from Brene Brown. In the past, I’ve let the women in my life see me fall off my white horse - and it didn’t go well. I can point to the exact turning point in my 7-year relationship when my then-girlfriend saw me fall, and things between us were never the same. I used to think I couldn’t trust women with witnessing my vulnerability. Now, I see it as a limitation that they are not even aware they have. I’ve mentioned before that Dr. Robert Glover, author of No More Mr. Nice Guy, refers to women as security-seeking creatures. Give a woman an opportunity to feel unprotected or unsafe around you, and she may never recover from that feeling.
For the moment, monogamish fits well with my bachelor lifestyle. She’s with me about once a week. We rarely talk on the phone. We can go an entire day without texting, although we typically have a daily brief exchange. I make plans without consulting her and vice versa.
Lastly, I’ve found my relationship limit: I am not willing to go deeper than I am with her, which is mostly about me and my desires rather than about her. Eventually, I will have to have that conversation with her.
Thanks for coming along for the ride.
Peace, Freedom and Progress
Your Squirter girl reminds me of the Nerdy Nympho girl I met early on—I bet you might have given her a number of orgasms on a similar magnitude as I did with the Nerdy Nympho, with how easy the Squirter could come. That’s really validating for us early on as we gain footing for our esteem.