woman in white brassiere holding red rose and menstrual cup

The Underwear Conundrum: Dating after 40

What is the Underwear Conundrum?

The underwear conundrum is one that all women face when dating someone new upon the first time that they are about to wear nothing other than a smile in front of their partner.

This concept was most eloquently outlined in the 2001 classic film, Bridget Jones’s Diary.

Yes, we all have a pair of tummy sucking in panties prefered by grannies the world over.

The thesis of this conundrum lies in the following conclusions:

  1. Wearing cute panties and bras are better when getting laid
  2. You are more likely to get laid when you’re wearing gross granny panties

This is true whether you’re a woman sleeping with a man, or a woman sleeping with a woman, or other identified person.

These are just hard facts. If you wear granny panties or period panties (yeah, I know) or boxer shorts on an early date, you’re at least 75% more likely to have a hookup occur.

Why boxer shorts? Well, hunty, I’m a girl who wears short dresses. I’m also a parent who bends over a lot. I don’t like my ass hanging out or my thighs rubbing together. Henceforth, I wear men’s boxers under many of my clothing items.

Why MEN’s boxers?

‘Cause they don’t make comfy ones for women. Boyshorts are bullshit. The only thing comparable is running shorts, and those are usually thicker and more obvious when wearing under a dress.

woman in white shirt and gray skirt standing near brown leather couch
Like seriously, make these for ladies, please. Photo by cottonbro on Pexels.com

I digress… back to dating after 40 and panties.

Here’s the thing about dating after 40. This girl doesn’t actually own cute panties anymore.

I own huge stretched out cotton panties that go up over my stomach and end right at my ribcage. (Referred to as my “pregnancy panties.” Because I bought them when I was pregnant with Peej.) I own men’s boxer shorts, and “period panties” (I know, shut up.)

I own exactly 4 pairs of panties that are black and that do not go over my stomach. These panties might be considered acceptably cute. It’s not the year 2000 over here, I don’t have thongs hanging out the back of my super low cut flare jeans or boy’s underoos like Cameron Diaz in Charlie’s Angels.

I’m 46 and have parented 2 children. No one wants to see that shitshow, literally.

I’ve been in a monogamous relationship for almost a decade. British Ex told me on our first date that he isn’t bothered by lingerie, that he finds it a waste of time.

pink brassiere on white table
Yeah like my workout gear is that well coordinated. Please! Where’s the ratty college t-shirt? Photo by cottonbro on Pexels.com

Then you have to take into account bras. When dating after 40 your tatas should be (likely) the main focus of your neekid experience.


I gave up cute bras for Lent in 2018. Look, I have ginormous boobs that have produced milk for two babies. These tatas touch my knees. I work from home. I don’t need anything more than a sports bra or a t-shirt bra. Come on!

This folds back into one of my primary issues with dating after 40 to begin with: Men seem to think you’ll have the same body you did when you were 25, regardless of how many up-to-date full body shots you post.

Uncomfortable Underwear = No

Honestly? Any man that thinks they’ll get me into a lace underwire bra is not the guy for me. Chicks are not so picky. They accept the t-shirt bra proposition.

Men? Not so much. Mostly because they need two hands and a flashlight to get a normal bra off. They freak out at trying to figure out a bra that X’s your back or goes over your head. (I’ve done in-depth research on this in years previous to marrying British Ex, so I speak with a knowledge base that is comprehensive.)

Plus there’s the whole uniboob issue. Women are more accepting of the uniboob proposition, because they have (at one time or another) had a uniboob themselves.

Men? They don’t like the uniboob.

woman covering her breast
Naughty! Photo by Andrea Piacquadio on Pexels.com

Dating After 40 + Body Dysmorphia

The larger issue with the underwear conundrum is that it lends itself well into my own body dysmorphia. I don’t feel comfortable in my own body. The one good thing I can say about British Ex is that he accepts and (used to) worshiped my body no matter what shape it was in. The idea of getting neekid with a new person? Frightening. Will they accept the big roll of flesh around my middle that exists from carrying two children? How are they going to feel about my boobs that fall under my armpits when I lay down?

What about my ass? I have a nice looking ass (in clothes,) but out of clothes they might notice my cystic acne or (if they go there) that I have permanent hemorrhoids from having two babies push on my internal organs.

women in white crew neck t shirt and blue denim jeans
Dating women is easier, in some respects. Photo by cottonbro on Pexels.com

Women are More Accepting of Other Women

I have found that when I am dating a woman, these issues don’t really come up as much. Because we have shared experiences with our bodies. They understand the period panties (okay, just deal with it) – stretched out comfy undies – and, boxer shorts.

In particular, they understand the way that our bodies change as we get older. They are more accepting of soft flesh, stomach rolls from having babies, droopy tatas. If they haven’t had them yet, they know they are coming for them someday. In some form. (Not all women want to be mothers. And, that is awesome.)

As I’m a “hearts not parts” bisexual woman, it makes it hard for me to just stick to girls. I would say I should, because it’s easier. But, then along comes some man who I think is cute and that I vibe with.

Sexuality is complicated, timey-wimey, wibbly-wobbly… stuff.

This Is All Theoretical

While the underwear conundrum is a real thing, all this is merely theoretical. Because, who is going to have sex with someone new in the shitshow of a year that is 2020?

Not me. I mean, I suppose that if they present me with a recent negative Covid-19 test, I might consider making out…

But, really.

Still, I’m sticking with the granny panties alternative. It will almost guarantee that I get laid when the time comes.

4 thoughts on “The Underwear Conundrum: Dating after 40

  1. Corey Scott

    So many reasons I am grateful for my wife, but never having to try to “date” again is one of the top. Trying to adjust who I am to attract a stranger is the worst. I’m much happier finding the right ways to fit perfectly with my one person.

    I hope your date goes well, Kate.

    1. Kate Post author

      Tall Drink of Water is a cool guy, so I know we’ll have fun. But, who knows if it will turn into anything? Frigging Covid.


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