Former Bachelorette and season 28 winner of "Dancing with the Stars" Hannah Brown asks potential suitors to name a fun and romantic activity they can do at home, and Michael Bolton performs a hilarious parody of "I Found Someone" to give her suitors some important clues.
Comedian, actress, and TV host Nicole Byer tests suitors by asking them, “If I was a frozen pizza, how would you get me hot?” and Michael Bolton offers his rendition of “Wind Beneath My Wings” to help the suitors figure out Byer's identity.
Carson Kressley from RU PAUL'S DRAG RACE is looking for someone with a sense of humor. Carson quizzes the suitors to come up with the perfect date while Michael Bolton performs a parody of “I Don't Want to Miss a Thing.
Rapper and songwriter Iggy Azalea asks contestants how they would feel about dating someone significantly more popular and Michael Bolton sings "Don't Stop" to help the suitors figure things out.
Star on stage and screen, Taye Diggs challenges contestants to describe the word 'love' without using the word 'love' while Michael Bolton sings a clever rendition of "You Are So Beautiful."
“Bachelor in Paradise” television personality, Demi Burnett, is looking for a loving companion no matter their gender. Demi tries to get to know the contestants by asking them what the sentence at the top of their dating profile would be. Michael Bolton sings “I'll Stand By You” to help the contestants predict Demi's identity.
“Modern Family” star Nolan Gould is looking for someone confident, charismatic, and passionate. Nolan asks the contestants what five adjectives their best friends would use to describe them while Michael Bolton performs a witty rendition of “What the World Needs Now.”
Gabriel Iglesias, stand-up comic and sitcom star describes himself as ‘cuddly' and asks contestants their favorite way to cuddle. Michael Bolton sings “Because You Loved Me” to help the women guess Gabriel's identity.
Supermodel Tyson Beckford is looking for an adventurous woman who has a great sense of humor. Tyson has spent a lot of time on runways showing off fashionable clothes and asks the women to describe an outfit they would feel most confident in while Michael Bolton performs a parody of “Let's Stay Together.”
“Baywatch” and “Singled Out” actress, Carmen Electra expresses she is into ‘vibes'. Carmen asks the potential suitors to describe their vibe in one sentence. Michael Bolton sings “Ain't No Sunshine” to help the suitors guess Carmen's identity.