| 100% | DARES | 5 | Challenges that start "I bet you won't ..." |
| 66% | DARES | 5 | "I bet you won't eat that" and others |
| 54% | DAREME | 6 | Response to "I bet you won't" |
| 54% | ABC | 3 | Start of a kids' song that ends "Next time won't you sing with me?" |
| 53% | DARE | 4 | "I bet you won't go bungee jumping," e.g. |
| 49% | DARE | 4 | "I bet you won't dive off the high board with your eyes closed," e.g. |
| 46% | ABCS | 4 | Song that ends "Next time won't you sing with me" |
| 45% | DAREME | 6 | "You think I won't try that?!" |
| 43% | LOVE | 4 | Nat King Cole classic that starts "L is for the way you look at me" |
| 42% | ADIA | 4 | Sarah McLachlan song of 1998 that starts with the statement "I do believe I've failed you" |
| 42% | ABCS | 4 | Subject of a song that ends "Next time won't you sing with me?" |
| 41% | HOISTEDAFEW | 11 | "Say, I bet you've ___!" |
| 41% | HEYLOVER | 8 | Grammy-winning LL Cool J song that starts "I've been watching you from afar for as long as I can remember" |
| 41% | BYER | 4 | "Why Won't You Date Me?" host Nicole |
| 41% | ARE | 3 | I won't use it, but you will |
| 40% | ABCS | 4 | "Next time won't you sing with me" song |
| 40% | LORD | 4 | "Oh __, won't you buy me a Mercedes Benz?" |
| 39% | DECAF | 5 | Joe that won't keep you up |
| 39% | DECAF | 5 | Coffee that won't keep you up |
| 39% | DECAF | 5 | Coffee that won't keep you awake |
| 39% | SNOW | 4 | Blanket that won't keep you warm? |
| 39% | DECAF | 5 | Coffee that won't perk you up |
| 39% | ARE | 3 | What you may have that I can't? |
| 39% | ARE | 3 | What you can take that I can't? |
| 39% | UMNO | 4 | "Yeah, that won't work for me" |
| 38% | DECAF | 5 | Brew that won't give you a buzz |
| 38% | DRAMA | 5 | Movie that won't make you laugh much |
| 38% | DECAF | 5 | Coffee that won't give you a jolt |
| 38% | VOICE | 5 | "Don't you take that tone of ___ with me!" |
| 38% | MEANDMYBIGMOUTH | 15 | "Oh, no! I shouldn't have told you that!" |