824 shares Esterman — who works in real estate — had on a navy blue blazer with a matching polo shirt and dark blue pants. The two first met on Williams' talk show when they played a dating game. Williams shared an Instagram of the pair from their day out and captioned it, 'Mike & I are having fun!! I'm glad he's a REAL gentleman.' They had already developed an affectionate rapport, and the TV star could be seen resting her forehead against Esterman's while they sat in the back of a car. During their virtual meet-up on her show's dating game, Wendy had joked that she liked Esterman's job as a contractor because it meant he was good with his hands.