In love with my (almost) divorced friend

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Dear Meredith,

I am in love with a woman who is going through a divorce. "Jane" and I are both in our early 40s, and have had a wonderful, platonic friendship for many years. I have always been attracted to her, but have never acted on my feelings out of respect for her marriage. I have occasionally socialized with her and her soon-to-be ex, but I always thought he was kind of a jerk and often didn't like the way he treated her. Nevertheless, I have never spoken badly of him or tried to interfere with their relationship in any way. One night a couple years ago, she got a little tipsy at a party and tried to get physical with me, but I was the one who backed off due to her inebriated state and out of respect for her marriage. We both laughed it off a few days later, and nothing like this has ever recurred.
A few months ago, her husband told her he wanted a divorce and walked out on her. Since then he has been insulting, demeaning, and emotionally abusive towards her. He insists there is no hope for reconciliation, and we both suspect he has another woman. She is emotionally devastated, and plagued with self-doubt. I have tried my best to be a good, supportive friend, and have not crossed the line or expressed my feelings for her. I only want what is best for her, even if that means getting back with her ex. However, this whole experience has made me realize how much I really love her. I can't help thinking that I would be so much better for her. I would be a loving, devoted husband who always supported her and made her my highest priority.

I realize what she needs right now more than anything is personal space, support, and time to heal. I know this would be a terrible time for her to get into a relationship, and that anything started under these circumstances would likely fail miserably. I am also petrified that if I act on my feelings, I will lose her as a friend forever. On the other hand, if somebody else comes along and snags her, I will kick myself for the rest of my life for not telling her how I feel.

What is the best way to handle this mess? How can I express my feelings without jeopardizing our friendship? How long should I wait before trying to start something with her? How do I support her through these difficult times without muddying the waters?

– In Love with a Pre-Divorcee, New York

This is a muddy mess, ILWAPD.

If you tell her how you feel, you risk confusing and alienating her. If you don't tell her how you feel, you might lose the opportunity to be with her.

My advice? Wait until you're 100 certain that this divorce is actually happening. If the split is legit and has been accepted by both parties, put everything out on the table. Tell Jane that you adore her as a friend, but that it's tough to be her objective sounding board because you also have romantic feelings for her. Tell her that you have no interest in pursuing a relationship with her if she's not ready, but that you need to be honest about where you're coming from. Tell her that you still think about what happened at that party. Tell her that you've been baffled about how to bring this up.
The thing is, there is no perfect time to tell her that you're waiting in the wings. She does need time to confirm that she's actually getting a divorce, but once that's settled, she deserves to know that her very close friend might be something more.

I won't lie -- you might lose her. But that's always been a risk. I'd rather you take the risk than kick yourself later.

Readers? Should he tell her how he feels? If so, when? Should he wait until she's already divorced and had some time alone? Would it be a risk to wait? Is this a real friendship if he has feelings for her? What about that night at the party? If you were Jane, would you want to know about the letter writer's feelings? Discuss.

– Meredith