Demi Lovato details her wild skydiving second date, plus, women share their dating experiences

Demi Lovato at the Third Annual "InStyle Awards" presented by InStyle. Photographed by Matt Winkelmeye
Matt Winkelmeye

Everybody knows there is nothing more awkward than a date; on the first one, you’re a bit nervous because of the pressure surrounding the first impression.

If you make it to the second date, you get to know your date better and open up about your experiences. Unlike the first date, many believe there are no rules to a second date because, at this point, both of you have established a connection that's enough.

It is, however, different when you are a well-known celebrity. Singer and actress Demi Lovato opened up on the Ellen DeGenerous show about her extreme second date, which included skydiving in Hawaii.

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Dating a celebrity means you need to assume there is absolutely nothing they haven’t done or experienced; therefore, the pressure to impress is even more immense. So, when Demi’s date found out she has never been skydiving before, he took it upon himself to make sure she crosses it off her bucket list.

“I was seeing somebody, and they invited me on this trip so I was super excited and they’re like, ‘We have a surprise for today,’ and I was like, ‘Okay? What do I wear?’ and they’re like, ‘Dress comfortable.’ So, I put on this silk jumpsuit with wedges, ready to go, and I walk out of the room, and they’re like, ‘That’s not comfortable. That’s not going to work,” she tells the host.

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The singer then found out she’d be jumping out of a plane for her second date, certainly not what the star expected as she wanted to wear a silk jumpsuit. “We go, and we jump from the highest point you can go without an oxygen tank, which is 14,000 feet (almost 4,3 km) or above.

We free fell for two minutes, and I couldn’t say no!”

Ellen followed up with an important question riding on everyone’s mind about if the relationship that took such a dramatic start worked out.

“They’re a friend! They’re a good friend. But yeah, no,” Demi responded, laughing.

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Below, other women share the wildest dates they've experienced:

I went on a date with a guy who asked me to meet him at the supermarket because he wanted to do some groceries before the date. I was so shook that I went along and helped him get the groceries. Why I didn’t leave, I have no idea.
Lelo
My date was an animal lover, so he set up our date at an animal shelter. I understand if I was the same, and honestly, maybe for the 10th date, it would have made sense but not as a first date. The dogs were barking everywhere, birds chirping all the time, we couldn’t hear each other. It was a mess.
Anonymous
I’m convinced I’ve been on a date with a robot. I met him online, and we went on two dates. On the second date, he repeated the same things he said on the first date, word for word. I played along at first, then I asked him about new things. He went back and repeated the same things. I still get freaked out by that date.
Anonymous
I’ve known him since we were toddlers; 15 years later, we decide to try dating finally. On our first date, he took me to his family braai. Everyone talked to me like I was his wife or fiancé, and I just wanted to get to know him
Chante
I love African cuisine but to expect me to eat with my hands on the first date is way too extreme for me.
Natasha
On our second date he invited me over to his place. I knew he lived with his parents, but I assumed they’d be away. They weren’t away. They kept coming into the lounge and giving us iced tea and chips whilst he played Xbox in his track pants (no shirt), and I sat there awkwardly watching. He didn’t speak much to me. It was 11 pm, and he was in his 30s.
Jessie
He told me he works as a creative. We went to a comedy show for our first date; little did I know, he was going on stage that night. He made a few racial jokes that made me so uncomfortable. To sum up the story, I left before the show ended.
Kea

Sources: E! Online, Billboard

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