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Oh, yeah. Marriage was not all about romance and your true love and soul mate and whatever until relatively recently. Families wanted their daughters to make good marriages, so if that meant an older man or even a widower, then yeah, that's who you are walking down the aisle with.
Also widowers - men getting married a second (or more) time because they need someone to look after their household and young children.
Kipling, in a funny poem, has the distaff version of that; young officers/company men in India flocking around older women (possibly because young men were not encouraged to/permitted to get married, taking native mistresses was frowned upon, so a flirtation or even affair with a married or widowed woman was one of the few sexual outlets, and if sufficiently old no chance of inconvenient and scandalous pregnancy):
My Rival
I go to concert, party, ball —
What profit is in these?
I sit alone against the wall
And strive to look at ease.
The incense that is mine by right
They burn before her shrine;
And that's because I'm seventeen
And She is forty-nine.
I cannot check my girlish blush,
My color comes and goes;
I redden to my finger-tips,
And sometimes to my nose.
But She is white where white should be,
And red where red should shine.
The blush that flies at seventeen
Is fixed at forty-nine.
I wish I had Her constant cheek;
I wish that I could sing
All sorts of funny little songs,
Not quite the proper thing.
I'm very gauche and very shy,
Her jokes aren't in my line;
And, worst of all, I'm seventeen
While She is forty-nine.
The young men come, the young men go
Each pink and white and neat,
She's older than their mothers, but
They grovel at Her feet.
They walk beside Her 'rickshaw wheels —
None ever walk by mine;
And that's because I'm seventeen
And She is forty-nine.
She rides with half a dozen men,
(She calls them "boys" and "mashers")
I trot along the Mall alone;
My prettiest frocks and sashes
Don't help to fill my programme-card,
And vainly I repine
From ten to two A.M. Ah me!
Would I were forty-nine!
She calls me "darling," "pet," and "dear,"
And "sweet retiring maid."
I'm always at the back, I know,
She puts me in the shade.
She introduces me to men,
"Cast" lovers, I opine,
For sixty takes to seventeen,
Nineteen to forty-nine.
But even She must older grow
And end Her dancing days,
She can't go on forever so
At concerts, balls and plays.
One ray of priceless hope I see
Before my footsteps shine;
Just think, that She'll be eighty-one
When I am forty-nine.
Yeah a big (if hidden) part of this story is the combination of the extraordinary reduction in childbirth mortality and the concurrent reduction in the "work in a dangerous male-only environment on the frontier for 10 years before getting married" life trajectory for men over the last century. Men would often get married later (to a younger woman), having returned to their poor home towns as impressive figures with money in their pockets to whisk away a bride from the local church social, then remarry (to a much younger woman) years later once the first died in childbirth, again organized by the local church, this time at the behest of the older ladies who couldn't stand to see the children grow up without a mother.
The comic reverse of that is the older woman who marries the younger man (often he marries her purely for her money), such as Chaucer's Wife of Bath who boasts of five husbands (at least, the ones she married, not counting any other friends she might have had) and the last is a scholar twenty years younger than her.
Or the Irish song Cailleach an Airgid which literally means "the hag with the money" and is supposed to be about a woman who went to America, made money there, and came home to get married, and having money she hooked a young husband.
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No, they really wouldn't. The vast majority of men in history were subsistence farmers who never traveled particularly far from their home and certainly didn't "work on the frontier" (except sometimes when that meant starting a farm on the "frontier" and staying there).
This may be a cultural difference. I'm from the American West and what I wrote describes pretty much every one of my ancestors from the 17th century through my great grandparents, and used to be a very common family story based on others I've talked to with similar backgrounds.
This dynamic existed in middle class Anglo families in America and England (making a fortune on the frontier or in the colonies) for maybe a hundred years. It barely lasted longer than our current modern dating dynamic,
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17th to 19th century American West was very much an outlier. I won't say similar things never happened elsewhere but they were a rarity. Even in the rest of America that was an exception as there wasn't a sizable body of people who expanded the frontier by conquest for an expanded length of time and then replaced the original people more than culturally. Ultimately the amount of wealth that can be gathered by that route for ordinary men is limited (almost as a tautology - where would masses of men they get such wealth from?)
It was fairly often the norm for the man to gather enough wealth to support himself and his family before getting married (although even that depended very much on the time and place) but that involved traditional boring stuff like working as a farm hand etc.
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