Would You Take the Do-over

I just finished a fun book, 90 Days in the 90s, in which an older millennial, upon her relationship in NY going south and her crypto portfolio blowing up, gives up on NY and heads back to Chicago to take over her recently deceased uncle's record shop. There she finds the time machine in the record store basement, so she heads back to 1996, to the days just before she bailed on Chicago and moved to NY.

I won't spoil the rest of the book for you, but it got me thinking.

If you got a do-over on college or your early 20s, would you take it?

I didn't have to think long. It's a big no for me. Yes, I know I'm passing on the opportunity to buy Apple stock for a dollar, and Microsoft stock while DOS is still state of the art. Our protagonist in the book retained her memories from the future, so I assume we would too.

I've shared the story of how I met my wife, but for any newcomers...we passed in a stairwell at a fraternity party. I was headed in with friends, she was headed out with friends. She and one of my friends knew each other from the dorm the previous year. If either one of is 15 seconds earlier or later in the stairwell we likely never meet.

So if I head back to 1987 or earlier, how do I make sure that meeting happens? I actually do remember the day of the party, so I guess I could lurk in the stairwell once the party starts. Because I'm sure a mullet-headed frat boy stalking her in a stairwell is a winning move with my wife. Of course, I'll remember her name, so in theory it would be easy enough to figure out how to meet her on campus. But again, the only way any of that works is if we are destined to be together. And I don't believe in destiny. A thousand things that are not repeatable happened that night that led to the spark that resulted in a 30+ year marriage. I don't know that us meeting the day before or the day after ends in the same result.

Also, am I the same person in the do-over? I'll be retaining all my future memories, so I'll definitely be making some different choices. Even if I did end up dating my wife again, any single decision I make differently could tank the relationship. Like, I don't know, dropping out of college in 1987 and investing all my college money in Microsoft stock. Telling her "Trust me, I'm from the future" probably isn't going to work.

If you buy the multiverse construct where every decision we make creates a new timeline, it seems like it would be completely impossible to reliably repeat history. For one thing, doesn't the mere act of going back in history change the timeline, not to mention all the other decisions you'll make differently?

Maybe it's best that we just not think about this stuff too much. Of course, if there are time machines, the people that know about it would want us to think that way, wouldn't they?