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1* AccidentalInnuendo: during Chance and Tango's fight, we get this exchange:
2-->'''Tango:''' (threatening Chance) I will bang you.
3-->'''Chance:''' Bang me, homie!!
4* CrackPairing: [[spoiler: Mr. Boston and Pumkin.]]
5* CreatorsPet: Tailor Made had shades of this in the second season. For example after spiting on Mr. Wise, instead of being eliminated (As anyone else probably would have been), he got to stay (But not without being forced to turn around away from New York during the Elimination Ceremony). Also, if Buddha is to be believed, there was [[http://www.shabooty.com/2007/12/31/ezra-masters-aka-buddah-buddha-from-i-love-new-york-season-2-claims-punk-tailor-made-bisexual-lovers.php some off-screen favoritism shown towards Tailor Made in the finale]][[note]]New York apparently told Buddha that she refused to spend the night with him because Tailor Made threatened to leave if she did.[[/note]] to the point where he wasn't really surprised that she picked him in the end.
6* EnsembleDarkhorse:
7** Mr. Boston is one of the most memorable contestants just because he seems to have the audacity to do ''anything'' despite not quite... [[EndearinglyDorky fitting the mold]] of the other contestants.
8** Other well-liked contestants within the house and among the fans included Whiteboy and the Stallionaire brothers, Real and Chance. The latter two even got their own spinoff called ''A Real Chance At Love''.
9* FirstInstallmentWins: Much like with ''Series/FlavorOfLove'' and ''Series/CharmSchool'', the first season was the more popular and widely viewed of the two seasons given the more varied and memorable contestants, no one in particular being designated as the obvious winner and the reunion show.
10* HarsherInHindsight:
11** In the first season episode where Real was eliminated, he and his brother Chance were so upset about having to leave one another, both men break down and start crying. This scene is now all the more harder to watch now as Ahmad "Real" Givens has passed away from cancer on February 21, 2015. May he rest in peace.
12** In the first episode of the first season, Tango tells both New York and Sister Patterson that he holds his mother very close to his heart, which both women like and respect. Considering what they said about her in the episode where the final three contestants brought their mothers to the house makes his eventual blow-up and dumping of her in the reunion show all the more understandable.
13** In the fourth episode of season two, New York showed that she really did care for Tailor Made a wee bit more than the other guys. She expected the better of him. So it's no wonder she was so angry at Tailor Made for spitting on Mr. Wise (it also reminded her of the time Pumkin spat in ''her'' face).
14* HilariousInHindsight:
15** It's "white people voice" where he shifts from an inarticulate weirdo to a preppy, bourgeois weirdo is even funnier after the premiere of ''Film/SorryToBotherYou'', some 11 years later.
16** 12-Pack running gag of being questioned whether he's a good fit for New York became even more hilarious when in the other dating show he was on, ''Daisy of Love'', he not only became a fan favorite but was voted by the other contestants in the penultimate episode that he should be picked if the others were not selected.
17* HoYay: 12-Pack and Heat. It's been noticed that they had more chemistry with each other than New York, which gets more pronounced post-show.
18* InformedAttractiveness: New York. ''Holy Shit,'' New York. Some would argue she ''IS'' sexy and attractive, just not worth a whole dating show.
19* JerkassWoobie:
20** New York at times, but the ending to the Season 1 reunion special especially.
21** Chance too, after New York [[spoiler: picks Tango over him.]]
22** Tailor Made is one to an extent. While he brought it down on himself to be a snitch and to be antagonistic towards the other contestants, he felt bad when he realized that nobody really liked him and he stated that he wanted to redeem himself. Anyone who's screwed up and made enemies and feels bad about it can relate.
23* {{Moe}}: Bonez. He was quite the NiceGuy, a real peacemaker, [[RealMenLoveJesus loved Jesus]] and reminiscent to a young Creator/TommyDavidson.
24* {{Narm}}:
25** Pootie’s FreakOut isn’t supposed to be funny because the dude is having a mental breakdown. This doesn’t stop fans of the show from making jokes about it. Pootie would later claim he was deliberately overacting to make good TV, but it's not clear if this is true or a ParodyRetcon.
26** Sister Patterson's singing in church. Apparently even the editors agreed, as they made it look like her singing was so loud, that it not only shook the building, but caused the "camera lens" to crack, too. One of the guys actually comments on her over-the-top performance, which leads to his elimination.
27* NeverLiveItDown:
28** Mr. Boston would always be known as the guy who got knocked out in the [[CurbStompBattle fastest way possible]].
29** The Entertainer would always be known for living in his parents' basement and sucking on New York's toes.
30** Pootie's FreakOut remains one of the most memorable moments of the first season, in spite of the fact that he himself didn't really stand out.
31* RetroactiveRecognition: This was Wrestling/DavidOtunga's first television appearance, as Punk, fresh out of law school. It's pretty safe to say he's done rather well from himself since then. He's a controversial figure in the wrestling community, but just about anything is a step up from here.
32* SoBadItsGood: No one's idea of quality television, but damned if its not entertaining. The trashiness is part of draw.
33* SpecialEffectFailure: In the infamous scene where Sister Patterson blew smoke in Chance's face, you can tell that some of it was CGI to make the cloud look bigger than it was.

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