"Date His Dad. Get Married." — Woman Befriends Situationship's Father at Airport
"You dodged a bullet."

Published May 16 2025, 10:30 a.m. ET

A woman who experienced a flight delay decided to strike up a conversation with a man who ended up being the father of someone she had a 3-month-long romantic relationship with.
Caroline (@ygdunlap) posted a viral clip delineating how a series of events led to her choice to talk to the man, and subsequent discovery of who his son was.
At the onset of Caroline's video, a text overlay reads: "you never know who you're sitting next to." Next, she begins to explain what prompted such a headline to her social media post.
She says that she was taking a flight from Washington D.C. to New York for a business trip.
And, in a trend that has become increasingly more common in recent years, Caroline states that she experienced a flight delay where she and her fellow passengers were on the tarmac well beyond the plane's scheduled departure time. So far past the scheduled departure time, in fact, that the airline staff informed passengers that they would have to be brought back to the airport.
While waiting on the tarmac, she decided to be productive and get some work in, combined with some doom-scrolling on her phone. However, boredom quickly set in so she decided to socialize with a fellow flier.
The aircraft was, as she describes it, a "two by two plane" and she was seated next to a man.
She said that he was "super nice" and was around her dad's age, in his late fifties or early sixties. Soon, they started sharing what brought each of them to Washington D.C. along with the nature of the work that they do and where they're from.
During their conversation, they were alerted to the fact that they needed to get off of the airplane and head back inside the airport. Upon disembarking, she contacted her company to let them know about the change in her travel plans and that she would need accommodations booked for her because she was stuck in Washington D.C. for the evening.

After leaving the plane, Caroline says that she spoke with the man, who says he spoke with his youngest son about the travel delay, on account of his son traveling often. He checked in on her, and the two of them opted to wait and see if the plane was going to board again before deciding to leave the airport.
She went on to state that the man was exceedingly nice, and even offered to purchase her some snacks while they stood and waited to see if airline staff had any announcements pertaining to their departure, or if the flight was going to be canceled altogether. Thankfully, the former turned out to be true and they were able to get back on the airplane without having to spend the night in Washington D.C.

After getting back on the airplane, to two continued their shared conversation, as they went about discussing "life and politics." Caroline says that she learned the man had spent a great part of his life being a firefighter. Afterward, the conversation turned to him discussing his wife and family, and she said he began to tell her about his children.
The man then informs her that he has two sons who, Caroline, for the purposes of the video, refers to as "Brian and Will" and that Brian had gotten married in the fall of 2024. He went on to show her photographs of "Brian and his new wife," before then showing her a picture of his youngest son, Will.
It was upon seeing this picture of Will that Caroline realized who the man she was sitting next to was: the father of a man she had a romantic relationship with.
"You guys. I see this photo of Will and I go I know this man, I know this man. It takes me half a second, I'm like rendering and I'm remembering and then I realized that Will and I had a three-month situationship the first summer that I moved to DC."

She went on to state, "And it did not end well. And not on my end and I'll leave it at that. OK? So then I have this moment where I'm like I just talked to this man for five hours. Me and him are buddies, like he knows me. I know him. Do I tell him, do I tell him I used to see his son?"
Not keeping her viewers in suspense for too long, Caroline determined that, indeed, the right thing to do was to tell him that they, in fact, saw one another. "Obviously I have to tell him. So then I say, 'Sir I don't know if this is appropriate to say or not. But I used to see your son.'"
As it turns out, they both found the situation to be funny, as Caroline said the two of them started "cracking up laughing."
She even went so far as to bring up Will's phone number in her contacts list and ask the man if he could confirm if that was indeed his number. Which he did.

After the plane landed, the two of them began to talk about it further. Caroline said that she was "tongue in cheek" about the way things ended because she wanted to spare him the details. At the man's suggestion, he said that the two of them had to take a picture, and Caroline agreed.
The TikToker correctly assumed that Will's father would go on to tell his son about the nature of their interactions on the flight. That's because, the following day, she received a text message from him which said, "Leave my dad alone."
Caroline says she opted to ignore the message and took one moral away from her story: Talk to strangers in the wild.
Commenters who responded to her story had a variety of opinions. There was one user on the application who suggested that she date and marry Will's dad so he would become her stepson.
Whereas someone else had another approach: "Leave my dad alone I would reply no YOU leave my bestie alone. See you at friendsgiving."