MTV News had the chance to sit and talk with the actresses about their own, often-public relationships and how their own dating plays out in multimedia culture.
Though Barrymore and Johansson both agreed that even bad relationships are learning experiences, Aniston knew exactly what she'd say if she could go back in time and give herself some dating advice.
"Never order a cherry tomato!" she said. "I was on a date with this guy ... there was a cherry tomato and he bit into it and it was all over my white dress. So that was just one side note. No cherry tomatoes!"
Scarlett had the hardest time coming up with negative dating experiences, explaining that, since high school, she had pretty much gone from one long-term relationship to another. Even through that, though, relationships become a learning curve.
"I think I've found that relationships are only going to work out when you're really yourself and you're not posturing in any way. You're just honest with who you are. ... There's a difference between compromising something and compromising yourself."
Added to the mix, all three women have had their fair share of trying to go on dates against a world of increasingly tech-savvy fans who eagerly await the slightest bit of relationship gossip.
"It's not fun," Aniston said. "You could end the date and shake hands with them and realize it doesn't work, and all of a sudden you're a new couple."
Though she agrees that prying eyes tend to get in the way, Barrymore relates celebrity dating to trying to go out with someone in any sort of public setting.
"I think it's the same as high school or inter-office dating. It's the same feeling. What we deal with is strange and surreal, but the emotions are the same as anyone."
Of course, most people don't have to deal with catching oftentimes fictional headlines about their dating habits at supermarket checkouts. At the slightest mention of tabloids, Barrymore was quick to point that she'll go to great lengths to never read them, while Aniston joked that if news of her long-rumored engagement does break, MTV News will be the first to know.
"I mean, that's actually at the top of my list. You're on the speed dial!"
But when all is said and done, Drew, Jennifer and Scarlett seem to agree that there's not a lot that separates the good and bad of dating for anyone. There's still the awkwardness, the misread signals and the sometimes just plain unrequited love, all of which they'll be bringing to the screen February 6.
Check out everything we've got on "He's Just Not That Into You."
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