I've often contemplated this.
If you've loved more than one person (say, you were a young widower who remarried and lived and long, love-filled life with someone else) who do you spend eternity with?
That is very problematic.
One of the reasons that I’m not enamored of re-marriage.
OTOH, it’s often said that Heaven is NOT what we think - worrying about the people we knew on earth. “Soul mates” are not sexual mates on earth, but souls who truly match well, regardless of sex or sexuality. So it could be your earthly spouse is just another soul in Heaven.
And thus, it wouldn’t matter how many you marry. (It certainly didn’t seem to faze the old guys, many of whom the last century + married many times.)
My wife would say you think too much too!! ;-)
The Bible says there is no marriage in heaven. So I imagine you’d spend eternity with both spouses, but wouldn’t be married to either.
If you have been married for 25+ years to the same woman, wouldn’t you rather try being single for eternity?