Hey! Jay! We were in another game together, but I don't think we actually played together? That'll be fun to remedy.
I super know nothing about the 100, but I've heard it's a wild ride. Natasha here (Romanoff, natch. MCU version) should be weirdly relatable to him, what with the reformed bad guy thing. She's also familiar with shitheads, so. That should go well.
Regina Mills, however (madamemayor), is not very tolerant of shenanigans at this time. Beware of her temper. Her bark is worse than her bite these days, but how just how much of a bite she has left remains to be seen.