The answer is, as always, yes AND no!
First off, a single Bolt will pull 32 amps. Two Bolts on the same circuit will pull 64 amps. If you have a 50 amp breaker, you'll blow the breaker. It doesn't "divide" the current. You can ASK any outlet in your house for a hundred amps, and it will GIVE you 100 amps until the breaker blows, which hopefully is really fast in that case.
YOU need to divide the current, or more accurately, tell your Bolts that they're only allowed to draw 25 amps each (less than that would be better) and that's the job of your EVSE (charger) - There's a chance you can set the max allowable current somewhere. I use OpenEVSE, so it's stupidly easy.
If you can set your charger current, then you can run two chargers off your 220V 50 amp outlet, provided that they actual wiring job isn't mickey mouse. Just because they put in a 50 amp breaker and a 50 amp receptacle doesn't mean that they ran cabling that's good for 50 amps, especially over the course of 8 hours. Or that the dopes even bothered to tighten down the screws on the breakers or the outlet. I've seen everything.
Also, solutions exist, Wattzilla comes to mind. It's based on the OpenEVSE, and it should be able to dial back and load balance two cars on the dual head unit.
https://www.wattzilla.com/options/current-share.htm
I'd even bet that once one car is done charging, it will tell the second car that it can charge at the full 32 amps. Email them and let them know that you want to split a 50 amp circuit and not a 100 or a 200. It' likely an easy change.
Even better than this would be to charge the high mileage car on the "big" charger and the low mileage car on the 110V. Least investment.
We're an EV only household here, and we just share the charger. My wife drives the e-Golf and she always charges, and I drive the Bolt and I charge whenever I can, but I could just as easily run on the 110V.
Good luck, don't let anybody tell you it's impossible.