13 Millennials Reveal Times They Took 'Playing It Cool' WAY Too Far


It was my sophomore year of college, and I was walking home with a boy I really, REALLY liked. He was older and therefore cooler than me, and I felt the need to be very nonchalant and cool in response.

On the way to his house, I saw a friend of ours from across the street. Feeling the need to prove that I was also friends with this guy, I started yelling, “JOEY!! JOEY!!” and running at our poor friend Joey like a total maniac.

While my crush waited across the street for me to finish talking to Joey, I started to wonder, How cool and hard-to-get would it be of me to just keep walking? Like, he’s totally expecting me to go crawling back across the street after this conversation with Joey because he thinks I’m obsessed with him, but if I just kept walking away from him, he’d be so into it. I’d be so mysterious, and it would create SUCH a chase. Needless to say, my grand plan did not work. Walking turned into awkward running, and he didn't chase after me like the men do in movies. He just kind of stood there, and we never talked about that again.

We all have stories like this. We've all tried so hard to play it cool that we've instead made things very, very awkward. It’s as much a coming-of-age moment as losing your virginity or going on your first date.

Unfortunately, the more you try to play it cool, the more uncool you end up looking. Unfortunately, most of us have to learn this lesson the hard way.

Don’t believe me? Just read these 13 confessions and see what I mean.

I didn't reciprocate oral sex because I thought that would make him want it more.

—Maddie*, 21

I didn't invite him to my date event, even though he was the only person I truly wanted there.

—Amber, 22

I slept with her roommate to make her jealous.

—Jim*, 25

I bragged about other options (that I didn't have).

—Zara, 29

—Megan*, 21

I encouraged him to date "the cute girl over there" when I really just wanted him to make a move on me.

—Nina, 23

I pretended to be f*ck buddies, but all I wanted was pillow talk.

—Alicia, 22.

I pretended I was fine around his new girl. In reality, the thought of her made me want to throw up in tinfoil and eat it.

—Alexia, 22

—Sheena, 25

I showed up way too late for our date, even though I was walking on clouds about being asked out in the first place.

—Kate, 22

—Eva*, 21

I was a b*tch to the last person I'd want to hurt.

—Gigi, 25

—Faith*, 21