Dating Diary #15

It's a Mixed Bag of Nuts

January 20, 2025

Dear Diary,

I’m back on my bullshit—did you miss me? When I tell you I’ve encountered a mixed bag of nuts, I don’t mean the salty, tasty kind you’d find in a bar pre-COVID; I’m talking about men. I know it’s been a while since I’ve shared a full-blown Dating Diary entry, so today, you’re getting a rapid-fire round-up of recent encounters.

Dearest Diary, these eight men—yes, EIGHT men—ranging in age from 47 to 59, matched with me on various dating apps between November 2024 and January 2025. Each one has made me question whether I’m god’s bravest soldier out here taking one for the team...or if I’ve completely lost my damn mind and need a vacation. The jury’s still out. Talking things through with you always brings me clarity, so let’s dive in.

Lazy Nuts

First, a quick PSA: there are plenty of other matches I’ve cut loose early on—men so lazy in their messaging they aren’t worth a paragraph, let alone a date. We’ll call them the lazy nuts. In fact, I’ve implemented a new rule to weed them out efficiently: if, after three back-and-forths, the guy hasn’t asked me a single question about myself or mentioned anything from my profile? Unmatch. Block. Done. I’m officially retired from conversational jazzercise.

We’re talking about adult men here—by the ripe age of 45 (my lower limit), they should know how to converse. I’m not carrying the whole load anymore.

Estranged Nuts

Okay, Dearest Diary, Nuts 1-3 don’t even get a fake name. Nut #1 invited me for coffee after a nice back and forth. N1 was 58, and on his second divorce, I knew there wouldn’t be a second date around thirty minutes in when he told me his oldest kids refused to have any contact with him. As the mother of two adult kids who are estranged from their father, that’s an immediate red flag. It goes without saying, but you know I will anyway; if a child makes the difficult decision to remove themselves from a parent's life, it means something significant. Kids don’t do that, especially adult kids, if a parent hasn’t done something entirely egregious to either the kid or their other parent. It’s just that simple. You may recall, Dearest Diary, my own mother was estranged from her abusive father—it’s never a decision a person makes lightly.

Boring Nuts

Nuts 2 & 3 were incredibly dull. I can’t even think of a nut bland enough to call them that. One wasn’t entirely divorced, only recently separated, which is also a no-go on my list of dating rules. N2 was a lovely man but boring, and I’m pretty sure Guy and Girlie would’ve scared the shit out of him had things progressed to the point of their meeting. N3 invited me to coffee, and thank goodness I ordered the smallest thing on the menu to expedite the date. I tried several conversational entry points and dropped multiple open-ended questions to no avail. Finally, I just stopped talking and let the awkward silence fill the space. He didn’t take the bait; he just kept looking at me, and whenever I’d make eye contact with him, he’d quickly look away. Finally, after consuming about half of my hot cocoa, I thanked him for the date and got up to leave. He quickly said it was nice meeting me, and he was going to his mom’s house to play with her dogs.

Cheap Nuts

This brings us to Nut #4, or Scooter, as I’ve come to think of him. Scooter was gregarious on the apps, and the conversation was easy. He’s an educator and reads a lot, so he was fun to chat with. After about a week or so on the apps, he asked me to dinner. We met at the local Mexican restaurant, which was if you recall, the scene of my first crazy date. I was pleased to see he was talkative in real life, too. It didn’t take long to realize, for the first time in my esteemed dating history, that I wasn’t carrying the conversation; I don’t think I’d said more than ten words since we sat down. This was not for a lack of trying on my part; I was just never able to finish a sentence. I suspected there wouldn’t be a second date, but that suspicion was sealed when the server arrived with the check.

Let’s take a step back for some groundwork, Dearest Diary. I never go on a date without the ability to pay my own way, and I always carry extra cash in case I notice the guy is a shitty tipper. Having said that, I’m of the school of thought that unless it’s discussed upfront, the person asking for the date pays. Especially the first date. I don’t think a man has to pay every time, and after the first few dates, I always offer, regardless of who set the date up. But date #1 is man territory; call me old school, but I don’t care; I have an ex-husband, and I’ve been called worse.

Back to Scooter and the check. The local Mexican place is $ - $$ at best, not a high-end fancy joint. Scooter and I had comparable meals, and we each had one drink of similar value. I set this scene because when the check arrived, Scooter stopped talking long enough to look at the bill and ask the server to take it back and split it according to our individual meals. The place was bustling, and I didn’t want to trouble the server with such a silly request, so I quickly offered to just split it and presented my credit card. Oh no, Scooter was not having that. We were each going to pay our own way, with no halvsies. Scooter seemed unbothered by this weird turn of events and kept right on with whatever he’d been talking about before the server arrived with the check. He could’ve asked for the split BEFORE she brought the check, no? I sat quietly as he continued talking when the split tickets and our credit cards returned. I watched ever so patiently as he proceeded to leave our lovely server a 10% tip on his $14.50 bill. He did the math to the penny.

Meanwhile, my brain was howling like Hozier’s primal scream in his duet in Noah Kahan’s Northern Attitude. Too niche, Dearest Diary? I paid my $14.38 bill with my credit card but without a tip. I loudly placed $25 in cash on top of my signed bill and gave him a look my kids would know meant trouble. Oblivious, he walked me to my car and was surprised when I stopped him like the Heisman trophy when he leaned in for a kiss. I texted him when I got home to let him know there wouldn’t be a second date.

Spicy Nuts?

Okay, we’re about halfway through these Nuts, Dearest Diary. As bad as Scooter was, he wasn’t even the worst of this bunch. I matched with Nut #5, Sandy, a little before Christmas. He was 59 years old and divorced for over 15 years with an adult child working on their PhD out of state. Things started out great; he was attentive and asked thoughtful questions. He also gave engaging and thought-provoking responses to my questions, not just one-word answers. We went on three or four dates, and all seemed well. He mentioned several times how much he enjoyed watching me talk with my hands. He said I had graceful, elegant hands that were quite mesmerizing. By the time New Year’s Eve rolled around, I felt comfortable inviting him to my place to ring in 2025. I told him upfront I was not ready for sex—I’m all about setting clear boundaries and expectations. He was okay with that and just asked for a kiss at midnight. No problem.

He showed up with tons of Thai takeaway that did not disappoint. He was not staying, and we were not drinking. Here’s where I tell you I now know when a man compliments my hands; it’s only a matter of time before he comments on my feet. Since we were in my home, we were not wearing shoes, but it’s winter, so we were wearing socks. Let the record show I was wearing cozy, wooly socks. After dinner, we made our way to the couch to watch the festivities and do a little making out. I need to reiterate that for the millionth time, I have regular feet. While kissing me, his hand made its way down my leg, where he slipped not one but both of my socks off. He stopped kissing me to admire my feet. If I’ve told you once, Dearest Diary, I’ll tell you a thousand times, a foot fetish is the most common of fetishes, and I’m amassing proof of this fact with each new date. Not wanting to waste a perfectly good New Year’s kiss with that particular discussion, I gently redirected his ministrations back to the kissing on the lips stuff. I should’ve just let the man fondle my damn feet. The next thing I know, my shirt is halfway over my head, and Sandy has homed in on my boobs. Left boob firmly in hand, he lowered his head and BIT ME. On the boob. Of course I yelled out, it hurt! He quickly stopped and looked at me with mischief (not the good kind) in his eyes and announced he “likes a little pain.” Still in his clutches, I informed him I do not like a little pain or any pain at all. That made him giggle, a 59 year old man giggled and dipped his head and BIT ME AGAIN. This time, I was afraid he’d broken skin. I jumped up and announced it was time for him to leave. He rather sheepishly semi-apologized and said he just lost control for a second and it wouldn’t happen again. I accepted his pseudo apology but kept my distance as he put his shoes on. While doing that, he told me he’d never hurt a woman; he’d only hit his ex-wife once, and she’d deserved it. These fucking men.

Days passed, and he texted to see if I was okay and asked if I’d like to get together again. I informed him I’d had a mammogram that day and had to explain to the technician that a man had bitten me twice, hard enough to leave very angry bruises on my left boob. He responded that he’d love to have been a fly on the wall to see how I handled that. I did not answer; I blocked him.

Racist Nuts?

Nut #6 is Ralph. Ralph was a 47-year-old professor. Divorced with two young kids, he’d only been in NC for a few years. We talked on the app for several weeks, and we actually planned a date, but life got in the way for me, and we had to reschedule. I was looking forward to meeting him; his chosen field of study interests me, and our conversations had been pleasant. He told me the week before our date he’d recently accepted a new role and had been doing a lot of new and interesting work coupled with some online study to prepare for his new position. He was excited to share details about this new role with me when we finally met in person.

I arrived a little before him, ordered a glass of wine, and had a clear view when he arrived. He was tall with blond hair, cut very short, and walked with a certain unmistakable confidence. Dearest Diary, I knew I’d been bamboozled as soon as he took off his sunglasses—you know the type—and tossed them on the table next to his black Otter Box encased phone emblazoned with a very specific flag. Sweet Jesus, save me now.

Ralph had indeed been a tenured professor with multiple PhDs for his entire adult life. However, he’d become disenchanted by his students since moving to NC and decided becoming a police officer would be more satisfying. He even went so far as to say he was sure he’d see most of his former students again but in a very different capacity. He said that with a tone that was soul chilling with excitement. He went on to tell me about how he’d met one of his supervisors earlier that day, and he was quite surprised by how “well-spoken” they were. Well-spoken, he actually said, “well-spoken.” Wow, dog whistle, much?

I was unsure how to extricate myself from this date. I certainly didn’t want to poke the bear, but I also didn’t want to stay on the date. I let him do the lion’s share of talking and practiced what I’d preached to my kids about keeping their mouths shut around law enforcement. After an appropriate amount of time, I made my way to close things out. I thanked him for a lovely date and got the hell out of there, sticking close to the speed limit! Should I maybe retitle this section ACAB Nuts, Dearest Diary? I texted him on the app the next day and wished him well in his new career, but I didn’t think we were an ideological match. He didn’t like that. I unmated and blocked him.

You know, you set your preferences on these apps. I do my best to make wise decisions. If you’re a paid member, you can filter out people you know aren’t a match for you; age range, distance, political affiliation, smoking, drinking, hell, you can even filter by height if you’re so inclined. But none of that works if people aren’t honest when setting up their profiles. Many very conservative men—I only date men, so that’s all I can speak on—label themselves as moderate and, in Ralph’s case, liberal. I don’t know why they do that? Why would you waste anyone’s time in this political climate? Is it a game they’re playing? He didn’t lie about his occupation; his new job was very new, and for all I know, he was still a professor when we initially matched. But, a big part of me thinks he was intentionally vague and misleading about his new “role” because he knew I wouldn’t agree to a date if I’d known the truth.

Double Your Pleasure Nuts

Twice now, Dearest Diary, I’ve double booked a date. While quite stressful, it’s easy to do on a Sunday. Early morning coffee to start and a lunch/brunch date after. That’s what I did one silly Sunday with Nuts 7&8. Here’s the thing: I know I’ve talked about having a roster in the past, but this is not what I was going for in this situation. You’re not exclusively dating someone when you haven’t even had a first date. This is just how the timing worked out.

Trip was my early morning coffee date. He was a 57-year-old scientist at a rival university. Interesting job and fascinating conversation. He’d been divorced for a long time and had no kids. I got the vibe that he’d been single for so long that he wasn’t looking to change that. It’s easy to get set in your ways after a while. From where I’m sitting now, Dearest Diary, that’s fair, and I respect it. Everything went well, and I enjoyed our time together. The conversation flowed so nicely that I put myself in a bit of a bind, timing-wise.

Funny story, I excused myself to the bathroom before we parted ways, and the line was rather long. I told the lady waiting ahead of me about my timing predicament. She laughed so hard and bowed down to me for being so brazen. She let me cut in front of her and even gave me a high five when I scooted by her on my way out. Girl power is strong in the ladies’ room, always!

It wasn’t a great date, but as you well know, I’ve had worse. Trip and I exchanged numbers and agreed to catch up later that evening to plan a second date.

Off to a late brunch with N8; let’s call him Burt. I feel bad calling him a Nut. He was a nice man, not nutty at all. Burt and I arrived at the restaurant at the same time, and he looked exactly like his profile pictures, which is always a welcome surprise. Burt was a 56-year-old finance guy who was very handsome in an innocent sort of way. Yep, I don’t know how else to describe it, Dearest Diary, very smart, very good-looking, not naïve, just innocent. Lunch went great; we took a walk afterward and agreed to see each other again.

Later that night, Trip called, and the conversation felt different. It was almost adversarial, like he was subtly trying to pick a fight. He leaned heavily into devil’s advocate territory with each level of our chat. I hate that shit! That’s not the sort of conversation I enjoy having. It feels like a test, is he seeing how far he can push me? I don’t know—he seemed like a different guy than the fella I had coffee with earlier in the day. We ended the call on a nice enough note, and I decided I’d give it one more try with him.

Meanwhile, things were progressing nicely with Burt. We spoke regularly and found a lot of common ground in some streaming shows we were both watching. That was fun. We had a couple more dates, but I think I made him nervous. To make it worse, he found my Substack, Dearest Diary. Ultimately, while very kind, things didn’t work out with Burt, and I think some of the things he read scared him a little. I get it. What I share on Midlife Rewrite can be a bit intimidating, especially the Dating Diaries. I’m realizing my writing might not be helping my dating life. I keep telling myself the man for me won’t be intimidated by what I’ve shared here. I’m okay with that.

I never had that second date with Trip. After a couple more text conversations that felt as unnecessarily heated as that ill-fated phone chat, I decided Trip, and I weren’t meant to be. I told him I’d enjoyed our time together but didn’t think we were a match. I wished him well and thought that was the end of that. He thanked me for being honest and not ghosting him and wished me well, too. About 15 minutes later, my phone pinged with another message from Trip, a real head-scratcher. Entirely out of the blue, he wanted me to know if I ever had an erotic dream and needed help working it out; I had his number. Where in the hell did that come from? We never talked about anything even remotely sexual, and certainly nothing erotic. Why Dearest Diary? Why would someone think that’s appropriate to say to someone who just said they didn’t want to see you again? What is in the water these men are drinking? They are fucking nuts!

Dearest Diary, we are into 2025, and I’m still confounded by these men I’m meeting. I don’t know what I’m doing wrong. If dating is a numbers game, as some people say, I’m certainly logging my time, and the odds do not feel like they’re in my favor. I’ve decided to stay on the apps until summer, and then I’m taking a break, perhaps a long break. It will be my 55th birthday gift to myself, peace of mind! Until then, I’ll keep trying and looking for love in what feels like all the wrong places!

Hugs and Kisses,

Donna

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