Sad trombone: 18 songs about awkward sexual encounters

1. Flight Of The Conchords, “Business Time” (2008)
Few things make sex as bad as a partner who isn’t paying attention to subtle signals, like the other participant saying “Eh, I think I’m just going to go to sleep. I have to work in the morning.” In Flight Of The Conchords’ straight-faced comedy song “Business Time,” Jemaine Clement takes on the character of one such oblivious partner, who’s mighty damn proud of his sexin’ skills, and doesn’t realize his boasts about his prowess and the weekly “business time” ritual (scheduled for Wednesdays, because “conditions are perfect / there’s nothing good on TV”) are erotic Kryptonite. Like when he counts brushing his teeth as foreplay. Or when he tries to take his pants off and trips over them because he hasn’t taken his shoes off yet. Or when he finally gets down to nothing but socks, and takes a moment to appreciate himself. (As Coupling taught us, “No self-respecting woman will ever let a naked man in socks do the squelchy with her.”) Finally, he gets down to business time itself, crooning, “Making love / making love for two / making love for twoooo minutes / When it’s with me, you only need two minutes / ’cause I’m so intense.” Two minutes later, “business hours are over,” and he lets his disbelieving partner know he isn’t surprised she wants more of him. Unfortunately, he’s so terribly tired. Then again, why exactly would she want more of that?
2. Randy Newman, “Maybe I’m Doing It Wrong” (1971)
From the Southern-gothic touches on Good Old Boys (featuring a nude exhibitionist purse snatcher and a hillbilly whose wedding night is spoiled when his unadoring bride “laughs at my mighty sword”) to the crooning “I Want You To Hurt Like I Do,” Randy Newman has created enough sexually and emotionally dysfunctional protagonists to populate his own clinic, and he once composed an anthem for them. “Maybe I’m Doing It Wrong” is a fumbler’s lament in which the singer struggles to find something in himself worthy of credit: “Sometimes I throw off a good one / At least I think it is / No, I know it is / But I shouldn’t be thinking at all.” Perhaps sensing that the number might be a little too on-the-nose, Newman originally released it on his little-heard 1971 live album; a studio version didn’t surface until more than 30 years later, when it appeared as a bonus track on a Rhino reissue of Sail Away.
Randy Newman – Maybe I'm Doing It Wrong [Studio Version] from Maldoon on Vimeo.
3. Elvis Costello, “New Lace Sleeves” (1981)
In the liner notes to the Rhino reissue of his 1981 album Trust, Elvis Costello describes “New Lace Sleeves” as being about “the tension between passion and the emotionally suppressing influence of ‘being civilised,’” which is evident in the song’s lines about “socialite sisters” whose fingers have “never seen working blisters,” and in all its references to the myth of British exceptionalism. But the theme of the song is best expressed in its opening verse, in which Costello describes “bad lovers” waking up next to each other and remembering how their fun flirtation at the start of the night turned into tedious, perfunctory boning. Costello expresses the distance between a sexy image and awkward reality when he sings, “Good manners and bad breath will get you nowhere.”
4. Richard Thompson, “Read About Love” (1991)
The lead cut from Thompson’s 1991 album Rumor And Sigh is a heartfelt plea for the importance of proper sex education. Thompson being Thompson, he makes his argument by vividly imagining just how fucked-up a person denied proper sex education could get. The singer relates how, when he was a child, parents and teachers shut him down when he asked them “what love really means,” so he was forced to seek out information from other sources: He “read about love” in such magazines as Cosmopolitan, Seventeen, and Hustler, as well as in a book “written by a doctor with a German name.” At the end, it turns out that he’s reciting this litany to assure the woman weeping in his bed that he truly understands “the ways of a woman,” and “if something’s wrong, then it must be you.” After all, “When I touch you there, it’s supposed to feel nice / That’s what it said in ‘Reader’s Advice’.”
5. Loretta Lynn, “When The Tingle Becomes A Chill”
Time was, most country songs tended to be about people wishing they could go to bed with someone they can’t, or regretting (or celebrating) going to bed with someone they shouldn’t. A year after scandalizing conservative country listeners with her 1975 hit “The Pill,” a rollicking tribute to the fun of having sex without the threat of adding another critter to the litter, Loretta stirred the pot again with this shockingly frank song (written by Lola Jean Dillon) about being obligated to have joyless sex out of a sense of marital duty, and smile about it. Lying next to her sleeping, contented husband, the wife softly cries to herself and confesses that “Although I pretend / You just don’t turn me on / The body performs / But the soul has no will.” She doesn’t see any light at the end of the tunnel, either: The woman clearly can’t imagine any way out of her marriage to a man she no longer loves or desires, so for her, nights like this are now just “part of the deal.”