How many times is too many when it comes to getting married?

This is subjective... but it depends on the reason.

'Till death do us part..."

If the spouse passes away that is one thing... obviously excluding foul play.

If it's just a person who is very indecisive and gets around... I'd say a 3rd marriage in my most humble opinion (which will disappear soon) starts to make things arbitrary.

Of course... there is that saying about a 3rd try in things.

My dad has only been married once and is still... but he is not loyal so... numbers are also just numbers.

It is hard to measure or ascertain the commitment of the heart.

Only nuances can show that and most people don't notice nuances for any subject under the sun. 

Do it right the fist time............ONE.

Five? 🤔       

I once worked with a woman that when I started working there had just begun her 4th marriage. Six years later when I moved on from the company, she was ending her 6th marriage. To answer the question, she should have stopped after the 2nd one.

4. One is really enough, but if it truly didn't work and you truly found someone else, I could see a second one happening. If the second one ended and the person gave up dating for a while (and not just jumped back in), then suddenly found someone but didn't let their guard down and was playing hard to get and with some EXTREME convincing, I would see a third one happening. But if a fourth one occurs, now it's like "alright, the marriage has lost its value. Maybe you work better with having FWBs"

First time around, she asked me and it went down in flames.

Second time around, I asked her and it went down in flames.

Two times is too many. Final Answer.

Everyone has to find their own formula.  Some people hit a home run the first swing, some people need a few at bats, and others know when to quit and hang up the cleats.

4                 

One time. UNO. 

Once.