When do I disclose my feelings to my almost divorced friend?

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I have a friend who’s in the early stages of a divorce. Some background: we met in college nearly 20 years ago. There was an attraction there, but at that time I made a stupid decision and dated someone else. She went on to marry someone else, get divorced, remarry, and is now divorcing her current husband.

I always told myself that if she ever became single again and I was single, I would make a move. I never thought I would have another chance, so now that it’s here, I’m stuck trying to figure out what to do. I never stopped caring for her, but once she got married, I didn’t pursue because I believe in the sanctity of marriage.

She’s that best friend you look for in a spouse. She's funny and nerdy like me. She has a beautiful mind (and body). What do I do? Do I tell her now how I feel, wait until her divorce is final, or wait six months after her divorce? I'm afraid of missing out on my shot because I waited too long.

I read a letter from a guy in a similar situation. The consensus seemed to be that he should wait until her divorce was final. I considered professing my love for her, and telling her that I would continue to be there for her and wait for her until she was ready to get back into a relationship. I really believe my chances are 50/50 at this point. I am worried that she won’t feel the same way, or that she has someone else in mind. But I'm not missing my shot this time. I just don’t know when to take my shot. To anyone commenting on my letter, please be kind. She is the person I would’ve talked to about things like this.

– Waiting

I'm not sure we can guess about timing here. Some people get divorced after months – or years – of the relationship feeling over. For others, it's more abrupt. The six months idea is pretty arbitrary, especially when you consider that the finalization of divorce is about paperwork, not feelings.

Start by inviting her to do some calm, one-on-one, date-night activities with you. See if she's open for more of your company. Then, whenever you’re having a good time, tell her you always hoped you'd have the chance to ask her out again, but that you're struggling to know if and when that's a good idea. Ask for her advice. But do try to read the room. If she seems overwhelmed, tired, or too in the middle of it to deal, hold your questions. The best time to talk is when it kind of feels like a romantic evening anyway.

Do not profess your love right now. Big gestures might seem romantic, but they're not always practical or empathetic. How would she be able to respond that kind of proclamation? All it does is raise the stakes, which are high enough right now. Also, it's a bit disingenuous to tell her you’re all in. You've never dated her. You might not like the experience as much as you assume you would.

If she tells you she’s not into this or not ready, respect her space. Continue to date others. But if she's not sure, let her know you're just throwing the idea out there. Tell her there's time to think.

– Meredith

Readers? Any thoughts on timing and delivery here?