woman in white brassiere holding red rose and menstrual cup

The Underwear Conundrum: Dating after 40

As I was drifting off to sleep last night, my brain fell back into happier dating times. Like, when you thought about what underwear you would wear on a date… in case, yanno. But, thinking about this topic led me to thinking about how the underwear conundrum affects women in their 40s. Especially women who have been married for a long time and haven’t had to rely on cute underwear since… well at least 10 years ago.

I have a social distanced date with Tall Drink of Water on Saturday. (What does that even mean?) You know it’s 2020 when you’re thinking about what mask best matches the outfit you’re going to wear on a date and wondering where your 6-foot measuring tape is. Not like things are going to get frisky Saturday. (They are 100% not, thanks Covid-19.)

As I have mentioned before, dating after 40 is rough. Honestly, at least 50% of the reason I got married for the 2nd time in the 1st place was so I didn’t have to date anymore. Because dating in your 30s was no walk in the park, either. Too many fuck bois and crazy ladies. Boo-hiss.

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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