"The Disgustings" (12:12 ) is a short film starring Drew Droege and written, directed and starring Jordan Firstman. It's about two gay men living in Los Angeles who just happen to be completely, utterly awful. The Disgustings return in "Save The Date." (5:45)
It was probably the cap on the toothpaste that did it. Matthew Flynn and Autumn Stein improvise a video that distils an entire relationship into 5 minutes.
It happens after you've ran out of things to talk about with your partner, after you get your sh*t together and have talked about plans for a family. It is time to get engaged, send out the invitations, and start planning the wedding. NSFW audio
From 1999 to 2003, the largely-female UK comedy trope Smack The Pony had a series of short skits based on video dating ads. Youtube user myLastTears has edited them together into a supercut: 1 - 2 - 3 - 4 [more inside]
Shut Up and Ride. A short video about breaking up.
YangTown, the Path of Masculine Power, [parts of the site NSFW] was created by a 25 year old guy in LA, who put together his ideas on dating and life advice. The site has a number of his articles on various topics that might be interesting to both men and women such as Are Any of These 5 Energy Vampires Draining Your Life? There are also informative links to Female Orgasm Mastery with explicit instructions on how to stimulate the G-Spot [NSFW], definitely [more inside]