After “We got a lot of funny looks”, maybe dig into the joke more. Get a quick, guaranteed laugh. “Turns out meditating in the library isn’t the
“My life is far better because of him” lands as a little trite. Maybe just end with “…encouraged me to reach higher.”
Most ppl won’t know what Radegast is - maybe just say “at a bar in Williamsburg”?
“She’s someone I genuinely enjoy spending time with” also lands a little trite.
Did you intentionally repeat the Monopoly Deal and “We’re going to be friends” bit?
The transition from “She’s sharp, competitive, …” to “That matters because Ittai has been extremely deliberate…” doesn’t make sense to me.
Maybe the link between the two is “they’re both pretty intense in their own ways, and that makes them a good match”
I think the Meghan section is a little generic - can you add another example? Was there a specific time she dragged Ittai out of the house and it was a great time?
Maybe this could be a good self-deprecating hook/joke at the beginning - something like “one thing you should know about me is I love examples. My girlfriend can confirm. She’ll say, ‘I love you’ and I’ll say, ‘can you give me an example of something I did that made you say that?’ So tonight, I’m going to give you a few examples of what makes Ittai, Ittai.”