The original hosts were Chris Hardwick and Jenny McCarthy. When McCarthy left the show in early 1997 to star in her own sketch-comedy series (The Jenny McCarthy Show), MTV hired Carmen Electra to replace her for the last season and a half.

Each game began with one main contestant, the "Picker", being escorted onto the set blindfolded in front of the 50 potential dates in the "Dating Pool" while the announcer described him/her. The Picker was then led to a seat facing away from the Dating Pool and further divided from the potential dates by a wall.

The Picker was presented with a board showing six categories, which ranged from physical attributes to preferences in love-making to leisure activities. They generally were expressed in a humorous style, often with various pop-culture references. After choosing a category, two or three choices were listed (for example, a category on hair might be divided into blonde [vanilla], brunette [chocolate], and redhead [strawberry]), and the Picker was asked to eliminate one of the choices. After eliminating a choice, all the contestants who fit that choice left the Dating Pool, in view of the Picker. This process was repeated until 5 to 8 potentials were left, at which point they advanced to the next round.

In the third season, a "Golden Ticket" was introduced, which allowed the Picker to save one eliminated player as he or she walked in front of him on the way out of the studio. This contestant automatically advanced to the semifinals. For episodes taped outside, the "Golden Ticket" was replaced with a "Golden Lifesaver", with the same rules.

At that point, the Picker asked a series of questions which ranged from Dating Game-style questions (example, "if you had me alone in a limousine for 3 hours, what would you do to me?") to stunt-oriented questions (example, hitting a paddle ball a number of times, with the female host relaying the potential date's performance to the Picker). If the Picker was satisfied with the answer or performance, he or she would "keep" the contestant, advancing them to the final round; if the Picker was not satisfied, he or she would "dump" the contestant, eliminating him or her from further play. "Dumped" contestants were not shown to the Picker as in the first round, but were instead marked with some sort of prop, such as a toilet seat around the neck, a bag with a sad face on it on the male player's head, or a pageant sash labeled "Dumped". This round continued until three contestants were "kept", or enough players were "dumped" to leave three. If the potential date received the golden ticket, then sometimes the host would show him or her to the picker.

The wall was removed from behind the Picker to reveal a walkway with several spaces behind him or her. The three finalists started on the back step, and were asked a series of two-choice questions. Each time a contestant's answer matched the Picker's, the player advanced one space on the walkway (occasionally, a question might be worth two steps); the first player to make it to the circle on which the Picker was sitting won a date with the Picker. In case of a tie, a final question was asked to the tying contestants, such as "How many girls did (Picker's name) say he dated last year?"; the contestant who guessed the closest without going over won the date.

After a couple had been made, the two contestants were placed back-to-back while Hardwick read a description of the winning player to the Picker; the contestants were then turned around to meet each other for the first time, and their trip and prizes were described to them by the announcer.

Two games were played per show, first with a woman picking from 50 single men, then with a man picking from 50 single women.

Several episodes were shown with out-of-the-ordinary rules, guest appearances, or other notable occurrences:

The show served as the basis for a book: MTV's Singled Out Guide to Dating (MTV Books, 1996) by Lynn Harris and J.D. Heiman. This tie-in advice book was actually two books in one, a "His" side (with Chris Hardwick on the cover) and, turned over, a "Hers" side (with Jenny McCarthy on the cover). In this book, winning couples were interviewed about their dates.