Hey guys! I’m fairly young for the message board but I figured you guys would be the perfect people to ask. There’s usually a problem with sitting around the living room or dining room table and not having a lot to talk about. I’m usually good with friends of being able to come up with good/provocative questions that open us up to talk for forever. I’ve kinda just fallen flat with the older members of our family though. It’s hard to get them to talk about the old days and how things used to be and their younger wild days without straight asking them. You kinda gotta draw them into it. You guys got any ideas? I’d love to really learn more about them and hear about their young days.
The username / post combo makes me reluctant to give you advice. You might find out things you’d really rather not know.
(That said, some people really, really dislike talking about the past if it involved hard times. Asking about specifics of jobs or family members that are less likely to be negative might open the gates a bit.)
BOOZE, lots of it!
Not kidding man, want the real story from elderly relatives? Get em liquored up first.
For you, personally? ‘How’s your mum’ might get a reaction 
I’m about to head to Mr Boods’ parents house in a little, 800-year-old village in Kent. ‘Is it true your mum didn’t have to change her name when she married your dad’ might liven up any lulls in the conversation this afternoon.
I’ve noticed that it’s better to ask about sonething specific rather than something general. My grandma (who is 95 and in possession of 100% of her marbles) tends to tell childhood stories if left to her own devices, because the Great Depression came along when she was 9. To hear about her life after the age of 10, you have to ask a specific question. If you ask “what was it like in the Depression” she’ll just say “hard.” OTOH, if you ask “do you remember a big Dust storm in 1934? Weren’t you in high school then? It was in the paper” – then you’ll hear quite an interesting tale about how topsoil from Kansas blew into NYC (and knocked down an elm in her street).
At a big family thing (not my family) someone stirred the pot with, “OK everyone, if you didn’t marry your spouse, who would you be here with?”
It was like watching the aftermath of a train wreck.
In a similar but less stabby vein than kayaker, I like to ask people what it was about their spouse that made them noticeable. I’ve had men in their 60s tell me their wife’s outfit down to the earrings; plus it could be the rare time a widowed person gets to talk about something sweet they recall about their spouse, rather than their illness or passing.