Dating A 25-Year-Old Feels Like Babysitting A Grown Man | Ginny Hogan

TOO Funny in Life
198 followers
3 Video Views·Aug 5, 2026
What happens when a 22-year-old hears you're 32 and says "that's okay" like you survived something? Ginny Hogan opens Regression with the brutal math of aging, falling for a 25-year-old who treated masturbation as a personality trait, and becoming the token female engineer at a vegan mayo tech startup where her best joke got her sent to HR. Fr …
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Video Summary
AI GeneratedA comedian reflects on her 20s, blending personal anecdotes about dating younger men with her professional experiences as a female engineer and data scientist in Silicon Valley. She satirizes gender dynamics in tech, the absurdity of corporate perks, and her failed attempt to use data analytics to engineer a happy life by age 30.
I'm doing okay. Thank you for asking. I've actually been feeling a little bit old recently.
A 22 year old asked me how old I was. I said I was 32 and she said, that's okay.
I don't feel old though. Like, I do young people things, okay?
I recently got dumped by a 25 year old. That's a young person thing to do.
I did recently date a 25 year old. That was a real test run for parenthood, I gotta say.
I spent most of the relationship looking for other women with much younger boyfriends
to go on a play date with mine.
And the relationship went well for a little while. I think one of the things that really
worked in our favor is that I didn't know a single other 25 year old.
So I assumed everything he did was normal.
Like, he talked about masturbation constantly and I was like, Gen Z!
So progressive.
But the only way I could talk myself into dating someone so much younger was
to remind myself that age is nothing but a number.
Numbers, unfortunately, are everything. They really are.
Money is a number.
And I'm a numbers person. I like math. There's this stereotype that women are bad at math.
But honestly, if men were smart, you guys would claim this stereotype for yourselves.
It would be a great excuse for lying.
Like, sorry babe, I'm not a numbers guy.
I really thought it was eight inches.
When I was 22, I followed my love of numbers all the way to Silicon Valley.
I moved to San Francisco and I became an engineer.
And the type of engineer I was, I was a, um, a female engineer.
My very first job out of college was at a vegan mayo tech startup.
I am that white, yes.
Vegan mayo tech startup.
Each word whiter than the last.
My co-workers at this company thought I was very funny.
I don't mean to brag, but I was once described as a hoot.
And they were the world experts on funny because they were, by and large, men.
Men are so funny.
Not the joke, but it's actually very convenient.
It's very convenient that men are so funny.
Like, sometimes I don't even get my own jokes until men explain them back to me.
I used to make this one joke all the time because I was very lazy.
I used to say, I can't get fired.
You can't fire female engineers.
I got called into human resources and the HR guy was like,
listen, Ginny, people are very upset about that joke.
And I was like, look, Nick, the audiences don't like it either, okay?
And he was like, as a man, I could tell you why.
But the real issue is that people think it's offensive.
And I was like, okay, am I going to get fired?
And Nick was like, no, we don't fire female engineers.
I did have to leave the mayonnaise company because of a privacy scandal.
Legally, I can't say more.
So I made the very logical leap after that.
I went to Facebook.
Please don't judge me, okay?
It was 2015, back when all of Facebook's data breaches were still secret.
It would be so embarrassing to work at Facebook today.
I hope none of you do.
But no judgment.
I recently had a hinge date planned with a Facebook engineer.
And the morning of the date, he texted me to say that Facebook just announced
a huge round of layoffs and his boss just put a meeting on his calendar.
And then he asked me if I'm still down to go on a date with a guy who doesn't have a job.
And I say, it's better than going on a date with a guy who works at Facebook.
I thought I was being very supportive.
Anyway, his boss was just checking in.
He didn't lose his job.
And he and I never went out.
But back in the year 2015, I was lured to Facebook by all the perks they were offering women.
Tech companies at this time start offering women the craziest perks.
Like at Google, they are paying women to freeze their eggs.
Less of a perk, more of a very pointed suggestion.
Did you talk to my mom?
If Facebook wanted to compete, their only option would be to do the abortion on site.
On the website.
I do think that the worst part about getting an abortion at Facebook, though,
would be one year later.
When they reminded you of it.
I worked with all men at Facebook too.
It was mostly bad.
There were some perks.
If I ever didn't want to work one day, I could just skip wearing makeup and they would send me home sick.
What are the wildest facts about men working with all of them?
Do you guys want to hear a crazy one?
Did you know that the way that a man looks when he wakes up in the morning is the way he looks
that day?
The whole day.
Who looks in the mirror in the morning and thinks this will do?
Sociopath.
I can't believe men make more money than us when you guys pee standing up in a line like you're
the Rockettes.
It's all just so shameful.
So my actual job title, I was a data scientist.
Companies paid me to help them make better decisions with their data.
However, I didn't stop the data analytics with my job.
When I was 22, I thought I could solve every problem in my life using data.
And when I was 22, I wasn't very happy.
But I had a very clear idea of how I was going to get there.
I specifically thought that I needed two things by the time I was 30.
I thought that I needed a partner with whom I could start a family.
And I thought that I needed a very stable career.
I thought that these were the only things I needed.
I thought that they were a necessary and a sufficient condition that if I had them,
I would definitely be happy.
And this is a stand-up comedy show about me trying to use data to achieve my goals.
But I just want to say before we begin, you do not need any math to follow this show, okay?
In fact, it's better if you don't know math.
Because liking math is for, say it with me, losers.
This is just a stand-up comedy show that goes linearly through my 20s.
At times, I have to break from the stand-up bits to tell you a little bit of story.
So if there is any part of the show, and I do mean any part,
that you don't think is funny, that's narrative.
Ties everything together.
Okay, so when I was 22, I already had a pretty good job in the tech industry.
The next thing I was in search of was a boyfriend.
A little bit on my sexual history up until that point.
Like many women of my generation, sex first came into my consciousness in the year 1998.
America had fallen in love with a young brunette by the name of Monica Lewinsky.
She was my introduction to sex, and she was a good one.
I recently saw a headline, it was a photo of Bill and Monica together, and it said,
Report, Lewinsky scandal took Clinton's eye off Bin Laden.
Imagine being so good.
