Amy and Ricky -- The Secret Life of The American Teenager
On The Secret Life of The American Teenager Season 1 Episode 1, good girl Amy Juergens discovers she pregnant after losing her virginity over the summer at Band Camp. Amy tells her friends that it wasn't romantic or like the movies, and she wasn't even sure it was sex until she got a positive on a pregnancy test. Considering this was Amy's first time and she didn't know Ricky all that well, it is no real surprise that her their encounter wasn't earth-shattering. This series was known for commentating on sex and the American Teenager. The awkwardness of Amy's first time was one of its best moves.
Leonard and Penny -- The Big Bang Theory
Leonard wanted to have sex with Penny since the moment he met her. His dreams come true on The Big Bang Theory Season 3 Episode 1 when the two friends/neighbors finally decide to become a couple and end the episode in bed. On The Big Bang Theory Season 3 Episode 2, they both express that while the encounter was "fine" or "okay," it wasn't exactly great. Going from friends to more than was weird for both of them. They talk about going back to being friends, but end up in bed together again and realize that sometimes you need to get over the hump.
Kemal and Lady Mary -- Downton Abbey
On Downton Abbey Season 1 Episode 3, Lady Mary Crawley meets Kemal Pamuk, and sparks fly. He comes to her bedchamber and seduces her, promising that nobody needs to know and she can tell whomever she marries that she is a virgin. However, while they are in the middle of the act, Kemal has a heart attack and promptly dies. This is possibly the most awkward on this list, because, well, death. Lady Mary must then move the body with the aid of her maid and her mother. Explaining why he is in her bed to her mother is awkward, but at least nobody else knows. Well, except Daisy.
Matty and Jenna -- Awkward
On Awkward Season 1 Episode 1 invisible girl Jenna Hamilton loses her virginity at summer camp to popular guy Matty McKibben. They do it in a utility closet. She tears up because it hurts, but she doesn't want him to know she's a virgin, so she tells him its allergies and to keep going. It was good enough for her still be totally into Matty, but when she tries to ask him out afterward, he tells her that nobody can know he likes her. Jenna puts her blog-staus up as "Rubbed Raw and Reeling" Rubbed Raw? It doesn't sound like the most comfortable of first times.
Ted and The Slutty Pumpkin (Naomi) -- How I Met Your Mother
On How I Met Your Mother Season 7 Episode 8, Ted finally tracks down the girl in the Slutty Pumpkin costume that he met at a Halloween party ten years prior. Both he and Naomi have been searching and waiting for each other for so long, neither wants to admit that things don't work between them. They are incompatible in all ways but especially physically. Ted tries to dump her but gets caught up in nostalgia, and they end up in bed together. "No part of it felt right," Ted told Robin and Barney, "at first there was too much eye contact, then not enough, where do you look during sex?" Finally, thankfully, the two admit their incompatibility and go their separate ways.
Dan and Blair -- Gossip Girl
On Gossip Girl Season 5 Episode 18, After being walked in on, or the awkwardness of Dan's Cabbage Patch Kid starring at her, Dan and Blair get a hotel room and get down to business. They both tell each other it was "wow," but later admit that it was terrible, mind-numbingly dull, and incredibly unsexy. Both fear that their connection is purely intellectual, but after a lot of alcohol, the two give it another go in an elevator and find that they are sexually compatible after all. As Dan said, sometimes you just have to throw out the first pancake.