With ALL of the available stable women in your age bracket, why would you even think about calling her again? I vote run.
Also, never, ever assume no means yes. Even if it does life is too short for games.
Finally, since you mention you’re a virgin I’ll give you the classic - but very valuable and very true - standard guy advise:
Don’t stick your dick in the crazy.
.
/thread
Guys, remember our meeting was nearly 6 months ago.
Depending on the circumstances of the divorce, she might still be a wee bit fragile.
There is absolutely no question whatsoever: move on. Do not go back.
If the first meeting had gone okay, with none of the tears and weirdness, but a second date never happened and THEN you found out she was asking about you, I would say give it a shot. But crying and refusing a second date, then asking about you quite a while later, are HUGE WARNING SIGNS. Advice to follow up on the HUGE WARNING SIGNS with an attempt at a second date is the sort of advice you find for free on the Internet.
WHAT? Dude, no. This is a no. Jesus…
Unless she has a damn good explanation for why she cried (just got bad news before your call; realized she tried to date too soon considering she had serious issues coping with the divorce that she feels over now), I would say don’t try again. It’s possible that she was just having an awful day that you ended up on the wrong end of, or she could have major problems. If you give her another shot, go into it with open eyes and extreme caution.
Ok. Sorry if I’ve misread the thread, but how do you know she was crying when you asked her out? It was a telephone call wasn’t it?
I don’t want to imply anything negative about you…but is there any chance that she was laughing? Or trying hard not to laugh and hurt your feelings?
Quartz,
One decent interaction back in September is not worth backtracking especially if she was at one point in tears, rejecting you in no uncertain terms. You made the first move. She turned it down. She probably asks about you because the woman dwells in strife and drama, or was just having a tough time coming up with conversation topics with your SIL. If she was seriously interested in you and has changed her feelings since nearly 6 months ago, she would call you instead of engaging you in a coy little game (which she isn’t).
I realize that your brother and SIL are casting doubt on your decision and they technically should know better because they’re in a relationship and you’re not but not in this case.
If you want to date, you need to actively date. If it’s take-it-or-leave it, this is a case of the leave it. Either way, this woman should not fit into your romantic plans.
Man, don’t all these dating threads end in condescending tough lough speeches? Has there ever been one where someone says “Yeah! Go for it! Pick a rainy night, but not too stormy, wear your most nonthreatening trenchcoat and blast Peter Gabriel from a boombox. Panty dropper, bro. Gettin it fo’sho.”
Then that prolonged interim is strike two. Strike three is her using SIL as an intermediary as if a kid in middle school.
All none of my damn business but since you asked for advice, it’s coincidentally exactly the same as the note I left for my milkman: “leave Quartz”
Don’t really know if she’s using the SIL as a go between. ‘Asking after [the OP]’ could have been simple polite chit-chat. ‘Hows your family. Is your BIL good?’, just to be nice.
Unless she specifically told your SIL that she wanted to hear from you, calling her again after she turned you down would be unbelievably fucking stupid. I can’t believe that anyone is suggeting otherwise.
Oh sure, you’d think that wouldn’t you? 
I re-read your OP after I posted my first response. I was debating on whether to repost but since you posted the above I will.
It’s been a long time. She has your email. She’s emailed you before. If she is interested (and sane), she’ll get in touch. Casually asking about you to the family doesn’t mean she wants to date you. If she is hinting to your family, move on. You don’t need that kind of childhood drama in your life. The woman has been married for god’s sake. I believe she has the where with all (and maturity) to contact you is she is interested.
But the bigger issue to me is why you haven’t let this go in 6 months. You are at the perfect age to be looking for dates. There are lots of divorced women out there. There are lots of single women out there. In six months you should have had plenty of opportunities to meet other women.
I don’t why you have dating issues in your life but I can assure you that becoming desperate enough to date crazies is NOT going to be worth it. If she was one of the last few women on the planet, OK make some allowances but as it is the world is your oyster, go fishing!
away from her. But run.
Anything less than an unambiguous yes means no. Don’t waste your time.
No, that’s not the worst that could happen. And I can speak with some authority on this.
The worst that could happen is she says yes and you have a great time and you find that she is smart and funny and very hot in bed, and best of all she seems to like everything you like, which is very hard to find in a woman because you have some unusual tastes. So after several months of great dates you marry her, and only then find out that she was able to control her crazy for short intervals, and was able to pretend to like the stuff you liked for short intervals, but has now decided that she doesn’t really like you or your house or your tastes in music or TV or pretty much everything after all, and proceeds to make your life a living hell.
Um, that’s what I’ve heard, anyway.
Tell ya what. OP, send me your contact info. I’ll hook you up with my ex-wife. If you take her out, I’ll pay the tab for your night on the town. What’s more, if you hit it off, I’ll pay for your next 6 dates. If at that point, you propose marriage, I’ll kick in three grand for your wedding/honeymoon, etc.
Please consider his serious offer.
Heavy alimony, huh?
As to the OP, I’ll just kick in the old saw: Never stick your dick in the crazy.
I don’t understand this story at all. You say she broke down in tears like it’s something unusual or concerning, but is one of potential reactions to someone asking you out on a second date. It makes as much sense as if she’d replied “ooga booga”. Then would you say, “She said ooga booga, should I ask her out again?”