Sometimes a first date teaches you that you really like someone.
Sometimes it teaches you that you definitely don't.
And sometimes... it teaches you to ask a few more questions before getting into someone's car.
Meet Cheapo Chuck.
It Was Supposed to Be Ice Cream
I was 18 and just starting to get involved with the Young Single Adults.
I was still pretty new to dating, so when a guy walked up to me after an activity and said:
“Hey, I think you're cute. Would you want to go get ice cream with me?”
Umm...
YES.
Someone thought I was cute. Someone actually wanted to take me on a date.
I was thrilled.
In my mind, this was going to be a simple ice cream date.
We'd talk. Get to know each other. Maybe flirt a little.
Except...
That is NOT what happened.
Apparently We Were Taking a Road Trip
Chuck drove an hour to pick me up.
And then we drove another two hours to meet up with some of his friends.
He had mentioned the plan, so technically I wasn't completely blindsided.
But I was 18.
I didn't realize “We're meeting some friends” meant:
three hours of driving.
Somewhere along the way, I also discovered he was seven years older than me.
I remember being surprised, but I didn't really know what to do with that information.
Remember...
I was 18.
I was young, inexperienced, and still figuring out how this whole dating thing worked.
When we finally arrived, though, the date was actually pretty fun.
We met his friends, got some food, did an escape room, laughed, and had a good time.
And finally...
ice cream.
And Then Came the Bill
While we were standing in line, I thanked him for paying for dinner, the escape room, and ice cream.
I expected a simple:
“You're welcome!”
Instead, he said:
“Well, it was kind of expensive. Would you mind paying me back for the escape room?”
Wait...
WHAT?
He had asked me on the date.
He had planned the date.
And now I was apparently being handed a bill at the ice cream counter.
At the time, I didn't really know how to respond.
So I apologized...
and Venmoed him the money.
Because apparently 18-year-old Alaina had not yet discovered the phrase:
“Oh...that's unexpected.”
Looking back, I can laugh about it.
I understand that dates cost money and that everyone has different expectations about paying.
If the expectation was that we were splitting the cost, that would've been completely fine.
I was perfectly capable of paying for my own activity.
What caught me off guard was finding out afterward.
And that taught me something pretty early:
Expectations are a whole lot easier when they're actually communicated.
Looking Back...I Wish I'd Asked More Questions
The money part is funny now.
But there's another part of this date that I look at very differently as an adult.
I thought I was going to get ice cream with someone.
Instead, I got into a car with a guy I barely knew and ended up hours away from home.
Thankfully, I was safe.
Nothing bad happened.
But looking back, I realize how easily that situation could have become uncomfortable—or unsafe.
I wish 18-year-old me had understood that it was completely okay to ask:
Where exactly are we going?
How far away is it?
Who will be there?
How long are we going to be gone?
And how am I getting home?
Having a plan isn't being paranoid.
It's being smart.
Especially on a first date, knowing what you're agreeing to—and having your own way home or a backup plan—is never a bad idea.
Because I thought I was getting ice cream.
Instead, I went on a three-hour road trip with a guy I barely knew.
Good thing there was actually ice cream at the end.
The Part I Didn't Understand Yet
There's something else about this date that stands out to me now.
At 18, I was so excited that someone liked me.
Someone thought I was cute.
Someone chose me.
And because I was so focused on that, I wasn't asking nearly enough questions about how I felt.
Did I actually like him?
Did I feel comfortable around him?
Did I like how he communicated?
Did I feel like I could speak up?
Did this actually feel like a good fit for me?
Sometimes we can get so excited that someone wants us that we forget:
We get to decide whether we want them too.
That was something I still had to learn.
I was focused on being chosen.
I wasn't thinking enough about whether I would choose him.
And that's a pretty big difference.
Not Everything Has to Be a Giant Red Flag
I used to think a red flag had to be something huge and dramatic.
But dating has taught me that sometimes the useful information is much quieter.
How does someone communicate?
Do they respect your time?
Are they considerate?
Do you feel comfortable speaking up?
And maybe most importantly...
How do you feel around them?
One awkward moment doesn't automatically make someone a terrible person.
And I don't think every uncomfortable moment has to become a giant RED FLAG!!!
Sometimes it's simply information.
Something to notice.
Something to ask about.
Something to file away under: Hmm...interesting.
What Cheapo Chuck Taught Me
If I could go back and tell 18-year-old Alaina one thing about this date, it probably wouldn't even be about the Venmo request.
It would be this:
Don't be so excited that someone chose you that you forget you get to choose too.
You don't have to prove you're pretty enough, fun enough, interesting enough, or easy enough to date.
You're allowed to observe.
You're allowed to ask questions.
You're allowed to have expectations.
You're allowed to say, “That doesn't work for me.”
And you're allowed to decide someone isn't a good fit.
Dating isn't just asking:
“Does he like me?”
It's also asking: “Do I like him?”
That's a question I wish I'd learned to ask a little earlier.
So if I had to sum up my Cheapo Chuck first-date advice?
Keep it simple. Know the plan. Have a way home. Communicate expectations. Pay attention.
And maybe most importantly:
Don't confuse being wanted with being well-matched.
Okay...tell me yours.
What's one lesson a first date taught you?
Because I have a feeling I'm not the only one whose “simple date” somehow turned into a story worth telling. ❤️
Sometimes the best thing you get from a first date isn't a second date.
Sometimes it's a lesson.
Sometimes it's a funny story.
And sometimes...
it's an escape room, ice cream, a Venmo request, and a brand-new dating nickname.
Cheapo Chuck wasn't my guy.
But he definitely earned his spot in the dating archives.
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