Male take needed on a dramatic suitor -- can this work?

We're taking a poll wrote:

Mid-40's trauma surgeon has been obsessed with my late-30's friend for the past 15 years. They were med school classmates. He took her on nice dates, would leave thoughtful gifts at her doorstep. They were never romantic. She liked him and could tell he was obsessed with her, but she was 23 at the time and felt he was a lot older than her...it just wasn't the right time for her. A year or two later, she ended up dating a childhood friend, whom she was with for the next 10 years. The classmate saw she was happy and went on his way...married a nurse type who had an special needs son from a prior marriage....married to her for 12 years now and has been a father to the son. He stayed in touch with my friend periodically over the years (maybe reached out once or twice a year with friendly words or to talk medicine). Started talking more when lockdown happened. She's been single now for about three years. He's become increasingly flirty and is now professing his love. She's said stop, you're married. He's persisted, so it's now a I'm blocking you, get a divorce, be free and single for at least (she'll decide six months to a year), then you can find a way to contact me, fly out, take me to dinner....I'll see you at six, bring the signed and dated divorce papers, I owe you nothing, we can go on a second date if the first one is acceptable.

Too many red flags with all the drama and fantasy? He's very strong and masculine, he's intelligent, he knows how to work hard and was in venture capital before medicine, so he has plenty of funds, may have had some military experience as well. He swears up and down she is the only person he has ever felt this way about, and his behavior has been consistent x 15 years. No way to know for sure, but he claims he hasn't had flings despite opportunities. Game plan above, but neither of us have enough mid-life experience to know how this will play out (it's oddly somewhat promising, but ^^red flags....). She was a mean H.S. XC runner and would win her races, definitely ran 19's, but I don't know PRs. No longer runs and has doubled in size. He is aware and unfazed. I am offended by obesity, but even with the extra weight, she is worth being obsessed about. Is there hope or will things fall apart when reality sets in?

We're taking a poll wrote:

Mid-40's trauma surgeon has been obsessed with my late-30's friend for the past 15 years. They were med school classmates. He took her on nice dates, would leave thoughtful gifts at her doorstep. They were never romantic. She liked him and could tell he was obsessed with her, but she was 23 at the time and felt he was a lot older than her...it just wasn't the right time for her. A year or two later, she ended up dating a childhood friend, whom she was with for the next 10 years. The classmate saw she was happy and went on his way...married a nurse type who had an special needs son from a prior marriage....married to her for 12 years now and has been a father to the son. He stayed in touch with my friend periodically over the years (maybe reached out once or twice a year with friendly words or to talk medicine). Started talking more when lockdown happened. She's been single now for about three years. He's become increasingly flirty and is now professing his love. She's said stop, you're married. He's persisted, so it's now a I'm blocking you, get a divorce, be free and single for at least (she'll decide six months to a year), then you can find a way to contact me, fly out, take me to dinner....I'll see you at six, bring the signed and dated divorce papers, I owe you nothing, we can go on a second date if the first one is acceptable.

Too many red flags with all the drama and fantasy? He's very strong and masculine, he's intelligent, he knows how to work hard and was in venture capital before medicine, so he has plenty of funds, may have had some military experience as well. He swears up and down she is the only person he has ever felt this way about, and his behavior has been consistent x 15 years. No way to know for sure, but he claims he hasn't had flings despite opportunities. Game plan above, but neither of us have enough mid-life experience to know how this will play out (it's oddly somewhat promising, but ^^red flags....). She was a mean H.S. XC runner and would win her races, definitely ran 19's, but I don't know PRs. No longer runs and has doubled in size. He is aware and unfazed. I am offended by obesity, but even with the extra weight, she is worth being obsessed about. Is there hope or will things fall apart when reality sets in?