Caitlyn Jenner Attempts To Get Back In The Dating World… As A Woman It’s been a while since Caitlyn came out as transgender, but in this struggly clip we realize all the plastic surgery and hair extensions in the world doesn’t mean you’re ready to play the field. Lastnight, E! Online shared a sneak peak of Caitlyn attempting to flirt with men and admitting that she fears rejection. It’s painfully awkward! Take a look and drop your comments below!
Taylor Swift may be a sweet, innocent girl, but she certainly does play the field. She's dated a lot of guys, however briefly, in her teens and 20s. Famous ones, to boot. T-Swizzle's love life played out on celebrity gossip sites and tabloids on a regular basis, and inspired hit songs galore. With her latest romance reportedly kaput, thanks to Calvin Harris' happy ending habit or Taylor Swift's squad , depending on what you read … … could another breakup anthem be in the offing?! In any case, Swifty's long list of ex-lovers just got longer, and man alive, it includes some doozies, and scandalous stories to boot. Here's a romance rewind for the ages! 1. Jake Gyllenhaal Not only did Jake Gyllenhaal allegedly take Taylor Swift’s v-card, he dumped her via text. TEXT. Then he proceeded to ghost her online. Pretty weak. 2. Harry Styles She knew he was trouble when he walked in … or so we’re told. 3. Joe Jonas This guy infamously dumped Taylor Swift over the phone. What a punk ass move from a dude who will probably rue the day. 4. Taylor Lautner Taylor Squared was a thing for awhile. If only we could go back to December all the time. 5. Conor Kennedy Taylor Swift was almost a Kennedy. Kinda sorta. She and Robert F. Kennedy Jr.’s son Conor were dating and very closely so, albeit only for a short while, back in the day. 6. Lucas Till Swift’s “You Belong With Me” co-star Lucas Till won her heart on the set of the hit music video, but their relationship was short-lived. View Slideshow
