Valentine's Day can be stressful enough for someone in a relationship. You'll find yourself Googling: "Chocolate or flowers? Do I need dinner reservations? How do you find rose petals? What is a bath bomb? Can I light candles on a wooden floor without setting my apartment on fire?"
But, for those who happen to be unattached, the day comes with different hurdles.
"Dear Kat, A guy I have been crushing on finally asked me out. I absentmindedly said I was free on the 14th -- Valentine's Day," the viewer wrote. "Is it weird to go on a first date on Valentine's Day? From, First Date on V-Day."
Barstool Sports' Pat McAuliffe told Timpf it's only weird if you make it weird.
"Yeah, see: He doesn't know it's Valentine's Day. To him it was Friday and that's it," McAuliffe said.
"You don't think about Valentine's Day until what?" he asked. "The day before Valentine's Day. I guess if you're in a relationship you'll think about it a little ahead of time. You've been crushing on him and he doesn't know it's Valentine's Day."
However, Timpf pointed out that if the viewer did not address the holiday, her date would think: "Oh no, she's crazy."
"You have to address it because he'll realize it eventually," she urged.
"And, people are going to know. When you go out to eat and you go to a restaurant people are going to know -- you're going to know on the date that it's Valentine's Day because you're going to be surrounded by couples," McCauliffe chimed in.
"But, if you've been crushing on this guy and you like him, who cares that it's Valentine's Day? You're getting a date," he continued. "This is what you want. Don't get in your own head and ruin it because a fake, made-up Hallmark holiday is putting expectations on what you should expect and what you shouldn't expect."
"If you're in your head about it... then you'll be weird. It's weird but, you know, it could be [...] a funny experience to have," Timpf concluded.