Tag Archives: body dysmorphia

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.

Little Itty Bitty Yellow Polkadot Bikini

Saturday, the Ex and I took Penelope to Leone Beach in Rogers Park to go swimming. One of us has taken her up to the beach or it’s attached park every day since it started getting nice out. In April, that was mostly the Ex, as I was still locked in my apartment on quarantine. Since Peej and I have returned from my parent’s house it’s been me taking her up there every morning between 9am and 11am (when she turns into an absolute crank monster.)

What I have not done is take her in the water to swim. First, it’s ice cold still. I’m a tough broad who loves to swim and I still shouted “fuck it all to hell” when I dove into the water recently. Second, Peej is fast as a cheetah and still has a hard time listening and following directions. This is a recipe for a disaster.

I definitely needed backup there if I wanted to take her into the water past her ankles.

Continue reading