Adam Pally took his shot when he got an opportunity to ask out Jennifer Lopez!
Back when the 36-year-old former Mindy Project star was a college student, he had to attend a taping of Inside the Actors Studio in order to graduate. After putting off the requirement, the only taping left of the season was with Lopez.
"I had to go to that and, I love Jennifer Lopez... but there's only so many answers to questions about the movie U Turn one person can take, so when the mic got passed to me to ask a question, I kind of blacked out or something and decided to do a bit," Pally recalled during an appearance on The Late Show With Stephen Colbert on Wednesday.
After calling the 49-year-old triple-threat star "J.Lo," and being asked instead to refer to her as "Jennifer," things continued to go downhill.
"I was like, 'I know that you've recently gone through a breakup with Casey Affleck'... To which she then quickly responded, 'Ben!' And I was like, 'Sure, sure, sure, sure,'" Pally remembered, referencing Lopez's infamous relationship with ex-fiance, Ben Affleck. "...So then I said, 'So, I've been through a breakup too recently. I don't know, I'm just feeling like we have a connection.'"
Pally didn't stop there! He then asked Lopez to watch a movie with him following the taping.
"I was like, 'So if you'd like to maybe, after your taping of this, I rented the DVD of the movie Big Fish.' It's so random. I don't know why! There was no Netflix and chill at the time," the Dog Days star quipped. "She was very sweet. She was like, 'Oh, no thank you very much.' And it didn't get a laugh, obviously, and I was horribly embarrassed."
Despite being horrified with his own behavior, Pally was relieved that he had met the requirement for graduation; at least until Inside the Actors Studio host James Lipton made things more cringe-worthy.
"Within three seconds of sitting down, Lipton had, like, a brain aneurysm explosion and was like, 'This is a serious class.' And I was like, 'Oh my god. Oh my god. I forgot,'" Pally recalled.
While things clearly didn't work out for Pally and Lopez, the Shades of Blue star has found love with former New York Yankees player Alex Rodriguez. The two have been sparking engagement rumors ever since the "El Anillo" singer started wearing a ring on that finger.
"I gave her the ring maybe four or five months ago," Rodriguez admitted on Wednesday's Today show in response to the engagement speculation. "I got her that ring. She loved it."
Rodriguez later confirmed that while the accessory has "significance," the two are not engaged just yet.
Back in March, however, a source told ET that Rodriguez and Lopez have "discussed marriage."
"They complement each other well. They are both driven business people with the same background and are passionate about their charitable efforts," the source noted. "Their families are now blended and live together."
Here's more on the power couple:
Alex Rodriguez Addresses Jennifer Lopez Engagement Rumors After Gifting Her With a Ring
Jennifer Lopez Opens Up About the Close Relationship Between Her Twins and Alex Rodriguez's Girls
Jennifer Lopez Gives Alex Rodriguez the Absolute Sweetest Birthday Wish