avatarJenn M. Wilson

Summary

The author, a woman in her forties who has recently separated from her ex-husband, reflects on her experiences with dating, particularly focusing on her feelings and interactions with two men, Jonah and Jeremy, while navigating the complexities of a new relationship and the fear of liking someone new.

Abstract

The author shares her journey through the world of post-divorce dating, highlighting her encounters with two distinct men. Jonah, who is attentive and available, represents the comfort of companionship, while Jeremy, who is newly single and embodies many of the author's ideals, presents a more complex and exciting prospect. The narrative delves into the author's internal struggles with vulnerability, the desire for genuine connection, and the challenges of balancing realistic expectations with the thrill of potential romance. Through candid anecdotes and self-reflection, the author conveys the emotional landscape of seeking love after a significant life change.

Opinions

  • The author is cautious about falling for someone new, preferring to keep her options open and being wary of red flags.
  • She values honesty and humor in a partner, as evidenced by her appreciation for Jeremy's ability to handle teasing and self-deprecating humor.
  • The author has a pragmatic approach to dating, acknowledging that no partner is perfect and that trade-offs are a part of dating in the modern world.
  • She is self-conscious about her age and physical appearance, particularly when it comes to intimacy and the fear of being compared to her partners' exes.
  • The author places importance on acts of service and practical help, such as Jeremy's willingness to fix her air conditioner and assemble her barbecue.
  • She is conscious of maintaining an image of being low-maintenance and independent, yet she appreciates

The Fear of Liking Someone New

It’s a cliché but falling for someone new is scary.

Photo by Dainis Graveris on Unsplash

Since separating from my ex-husband, I’ve dated endlessly. I’m not the type who can’t be without a guy; I just want someone to occasionally buy me dinner and call me pretty. And bang me.

I’ve rarely fallen for a guy. Every man is a placeholder until someone better comes along or they flash all the red flags. My MO is to date two guys at once since a single person is incapable of checking the bare minimum checkmarks.

One guy might be great at sex but the other guy has his life together. One guy might be hilarious but the other one is consistent with communication. One might be willing to marry me off the bat but the other has a solid career. These tradeoffs are the occupational hazard of dating in this new world.

Jonah is wonderful to me. He doesn’t see his kids (one red flag of a few), so he’s got all the time in the world to hang out. He’s in his early fifties and being in my forties, I look like the hot young thang on his arm. The dude’s got a good job and looks good naked. He fucks like a stallion but I loathe his face stubble.

I know face stubble doesn’t sound like a big deal but my old face is slathered with prescription wrinkle cream and it’s delicate like a butterfly. I hated making out with my ex-husband because of his stubble, I sure as eff am not going to suddenly enjoy it with someone who isn’t my kids’ dad.

The last time I saw Jonah, I got blemishes on my face that I haven’t seen since I was 20.

And then there’s Jeremy. Sigh. Jeremy.

We texted for weeks before the meeting because he was on a fishing trip with his son in Alaska. It’s a far cry from other men I’ve dated whose trips are always to one place: Las Vegas.

Jeremy is extremely good-looking. Take Justin Timberlake from his NSYNC days and imagine an older brother. He has gorgeous blue eyes and a dimple on one cheek. His body is flawless. His teeth are the best of any guy I’ve dated and if you’ve read my stories, you’ll know that I’ve whored myself out to many a guy.

Because no man can be the total package, that must mean he flips burgers, right? Nope, he’s an engineer at some building construction blah blah blah company. He lived for years in Canada and is now temporarily renting a house close to the ocean.

He’s funny as fuck. The majority of guys are serious, even the ones who think they’re funny. Jeremy can handle teasing and self-deprecating humor. That’s what makes guys like Ryan Reynolds and Dwayne Johnson attractive; their confidence shines through their willingness to poke fun at themselves.

Even better, he thinks I’m funny. He asked me if I write anywhere because my writing is hysterical. I told him that I write on Medium but it’s anonymous (I don’t let guys I date read my slutty tales). His response? “Good. You’re a great writer, that makes me glad that you’ve got that out there.” It seems my dazzlingly witty texts succeeded in making him interested.

I swear, I’d let Jeremy do anal if he asked. That’s how much I like him.

In my attempt to be realistic, I’m looking for those red flags. First, he’s only lived back in California for barely two months. What if that means he wants to bang loads of other women as part of his arrival? He can’t possibly think, “Just landed at the airport, time to settle down with the first woman I date!”

The next red flag is his split from his ex-wife is fairly recent. Their divorce went through in June. After some Googling, I found his wedding date: August 18th, 2000. In a week, it’ll be his first wedding anniversary after divorce. That milestone was tough for me. I don’t know if he’s indifferent or if it impacts him.

It doesn’t help that his ex-wife was a Pilates instructor who is now an “intimacy coordinator” for movies and their sex life was the one issue where they never had problems. This is all derived from passing comments here or there. Jeremy isn’t bragging about his ex-wife in any way. It’s just matter-of-fact.

I can’t compete with a sex expert with a Pilates body.

The biggest red flag, which isn’t a red flag as much as an annoying concern, is my lack of understanding of what Jeremy wants in a relationship. Typically, I have zero fucks to give because I know that I’m going to bounce first. Otherwise, men like Jonah make it crystal clear they want a partner by their side.

It’s too early to ask Jeremy. I know men well enough that they need to express their intentions first, otherwise they’ll feel pushed into a corner like a feral cat. The more I act like I’m chill and fun, no pressure, the more he’ll respond.

In other words, I’m singing “don’t be suspicious” on repeat in my head when it comes to Jeremy.

I’m not sure I’m doing a good job at being stealth.

It’s Monday and I’ve had my kids all weekend. My ex-husband lost his job last week and his lack of finances impact me but I make one last exception to having my cleaning lady do her thang with my disaster house.

Jeremy is coming over. I avoid men coming to my house because I try to avoid murder as much as possible but when I do, I barely make effort to clean. But this is Jeremy. The man I unrealistically put on a pedestal. I spend the entire day washing my bedding and trying to hide random dumb shit I don’t want him to see that might be a boner killer, like laundry baskets.

When he arrives, I give thousands of disclaimers. My couch has two layers of covers on it because my kids are messy and I’m not messing around with a Pottery Barn couch. My dining room is a converted playroom so it looks weird with large furniture from my old house crammed in it. I keep going until he says, “You don’t need to give disclaimers. People with kids get it. Our houses look crazy.” Bless his heart and his sperm that produced four offspring.

We drink wine and he asks about my now-repaired broken air conditioner situation. Jeremy goes into my garage to inspect the condensation line and gives me all sorts of engineering speak about fumes from the furnace leading out to a pipe through my ceiling. Do I understand any of it? No, I do not. But here’s a man who actively wanted to know what was going on with a major appliance and is trying to explain it to me. My God this man is sexy.

On the couch, we continue chatting nonstop. I ask him if I can show him a scene from this season’s The Boys (the one with the guy who shrinks and goes into a penis…if you know, you know) because I’m dying to see a man’s reaction to seeing it for the first time. Jeremy happily obliges and his reaction is exactly what I’d expect: he starts howling how he’s in pain between his legs from watching. I’m swooning that he placated my weird request.

Before leaving for dinner, we have sex. Earlier I smushed a boric acid suppository up my girly bits because in my old age, I’ve discovered that I need to do that occasionally to make sure it’s not gross down there. I thought I had enough time for it to fully dissolve but I can see the white goo on my comforter as he pulls out. Now I’m afraid he thinks I’ve got a weird vagina because who knows what that felt like inside.

Jeremy drives us to dinner at the one whole semi-nice restaurant near me that isn’t a Del Taco or Red Robin. He always opens the door and holds out his hand for me to climb into his massive Toyota Truck. Unlike Thomas’ ginormous Jeep that required me to climb into it like it’s Mount Everest, Jeremy’s truck has a step that comes out when the door opens.

Every time I place my 4" heel on that truck’s step, I internally gripe at Thomas’ Jeep. Whoever invented the ledge-that-expands-when-opening-the-door-so-it’s-not-a-drop-to-your-death deserves a medal.

When we order, Jeremy is in favor of ordering tons of appetizers instead of dinner. A man who loves appetizers more than dinner? This man is perfection. We talk nonstop without any awkward pauses. When the check comes, he refuses to let me pay despite that he’s paid every other time as well.

As someone whose ex-husband lost his job and is still getting used to one income, I very much appreciate when a man pays. I put my wallet back in my purse and thank him.

Driving back, I mention my new barbecue is still in the box in my backyard. It’s the bane of my existence. Assembling furniture is one thing, assembling something with gas lines outside in my backyard is a whole other ball game. Jeremy says he wants to see it.

We park and I make a passing comment that my neighbors probably hate me for leaving my trash can visible in my driveway. Jeremy immediately grabs it and starts rolling it into my backyard for me. As a woman who hates asking a man to do anything, this added another notch on the checklist of all things he’s doing right.

Looking at the barbecue box, Jeremy breaks it open and grabs the instructions. “You opened that thing like a Neanderthal!” I jokingly yell.

Inside my kitchen sipping more wine, he tells me we can assemble it tonight in my living room since all parts are clean. “You’re insane,” I tell him. “How long will that take?”

“Well, it will take me about an hour. For you,” he delicately pauses, “a bit longer.”

“How kind of you to not flat out say that this will take me hours,” I jokingly reply. I appreciate that the guy with an engineering degree didn’t make me out to be an incompetent female. Internally, I’m swooning that he wants to help me build this barbecue because he knows I’m struggling to even start.

Jeremy asks to see which tools I have and I lead him to the garage. He’s impressed by my cordless drill (I’m not fucking around when it comes to my heavy-duty DeWalt). The next thing I know, I’m bent over my laundry machine and we’re having sex again.

I tell him to bone me on the gym mats because I want to watch him fuck me. He obliges. Jeremy looks good in the mirror. He has a boy-next-door appearance and yet looks ruggedly handsome when his dick is taking over my body.

We throw our clothes on and head back to the kitchen for more chatting. I give him a glass of water and when I notice the glass is empty while talking, I immediately refill it. It’s my attempt to subtly show that I’m a caring chick who will satisfy his needs in and out of the bedroom.

Shortly after nine, Jeremy calls it a night. It’s a stupidly long trek back to his place because there are so many lights getting to my house. What should be a ten-minute drive easily takes thirty or forty minutes.

“Be cool, be cool, be cool,” I repeat in my head. “Don’t immediately text him. Let him message you that he’s home. Then thank him for dinner and tell him what a great time you had. Do not tell him that you’re smitten or low-key obsessed. Do not tell him to pretty-please be your boyfriend and that he’s so pretty you can’t stand it.”

When Jeremy sends the requisite I-got-home-safe text, I thank him for dinner and for making the long drive to my place. Then I say, “I adore hanging out with you.”

That’s my ninja way of putting “adore” and “you” in a sentence without looking needy, clingy, or that I’m moving too fast. Jeremy took his dear sweet time asking for my phone number (most of our pre-first-date chats were via the Hinge app) and even more to ask me out. I’m going to let him and his feral cat ways dictate the speed of this potential relationship.

The last thing I want to do is scare him off. Perhaps my Avoidant personality type is drawn to someone who isn’t throwing himself at me out the gate. I feel like a teenager when I think of him, full of butterflies and endless thoughts of him while I stalk him online because I’m crazy like that.

It’s Tuesday. My date with Jonah. The night before, he messaged about how excited he is to finally see me again and adds the emoji with the kissing heart. I should be excited. He’s wonderful to me, he treats me like a queen and is patient with my custody schedule.

He messages me asking if I’m spending the night. In all my whoring and dating escapades, I’ve never slept next to a guy. Not in my bed and not in theirs. I’d rather swallow a bowl of rocks before sleeping next to a guy.

I feign an excuse. Spending the night is too intimate. I’m not putting all my eggs in one basket with Jeremy so I try to keep an open mind about tonight. Limerence isn’t the only thing that matters in a relationship. I like knowing where I stand with Jonah and there are no guessing games.

But damn…the butterflies I get with Jeremy feel so good.

Sex
Love
Dating
Divorce
Self
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