Board Thread:Speculation House/@comment-27121579-20151117081605/@comment-4010415-20170225081132

73.Anon.52 wrote: Winter attended another academy too, we know Qrow went to Beacon and Winter to Atlas's academy, though this doesn't mean he wasn't there... for all we know he could have been in the area on a mission and done missions with students as a huntsmen.

I'm pretty sure they didn't date, though.

Winter isn't much older than Weiss, as we can see in the Schnee family portrait. So, Winter is likely in her early 20s 'cause she's probably only a few years older than Weiss.

Qrow is at least 38 or 39 because he and Raven are twins, and if Raven had Yang while she was 21, then 21 + 17 = 38, which would make her and Qrow about 38 in volumes 1-3.

It's hard to tell how old Weiss is in the painting, but if we guess that she's 10, then Winter would be 14 at the very least (and honestly, she doesn't look much older than that). It would also mean the painting was made 7 years before volumes 1-3, so Qrow would be 31.

It's actually quite possible and likely that Qrow was in his 30s while Winter was in her teens, so if they dated in the past, it would need to be the very, very recent past with Winter in her 20s.