I’m confused here, what you describe does not look like a random event, but a random resolution.
Of course a random event can have a random resolution!
Assuming you really describe a random resolution you can have something like this:
I’m proposing multiple passages to offer you a chance to describe environment and reactions better than a loop.
Passage FirstTry
Descriptive text of the scene
<<set $Money -=10>>
<<if random(1, 2) ==1>>You manage to lift the bear to the air all the way.
Ana is very happy!<<set $Toycaught to "Success">>
[[Leave]]<<else>>You fail miserably and Ana is not very happy!
[[Would you like to try again... at a cost of $10?|SecondTry]]
[[Better to give up while you still have money|Leave]]<</if>>
Passage SecondTry
Descriptive text of the scene, adding some sense of impatience from young Ana.
<<set $Money -=10>>
<<if random(1, 2) ==1>>You manage to lift the bear to the air all the way.
Ana is very happy!<<set $Toycaught to "Success">>
[[Leave]]<<else>>You fail miserably again and Ana can't believe how clumsy you are.
[[Would you like to try again... at a cost of $10?|ThirdTry]]
[[Better to give up while you still have money|Leave]]<</if>>
Passage ThirdTry
Descriptive test of the scene, Ana should probably grow really impatient,
maybe starting to comment on your obvious lack of skill.
<<set $Money -=10>>
<<if random(1, 2) ==1>>You manage to lift the bear to the air all the way.
Ana is very happy, and somewhat relieved!<<set $Toycaught to "Success">>
[[Leave]]
<<else>>You fail miserably still and Ana starts to look to think you won't make it.
[[Would you like to try again... at a cost of $10?|FourthTry]]
[[Better to give up while you still have money|Leave]]<</if>>
Passage FourthTry
Descriptive test of the scene, Ana might not expect any positive outcome
at this point, probably dejected because of her great sister failing again and again.
<<set $Money -=10>>
<<if random(1, 2) ==1>>You manage to lift the bear to the air all the way.
Ana is very happy! She can't believe you made it and wildly jumps all around you.
<<set $Toycaught to "Success">>
[[Leave]]
<<else>>You fail miserably and Ana is not very happy!
She tells you blankly you'd better to stop now, it's obvious you won't succeed.
<<set $Toycaught to "Fail4">>
[[You follow her advice, utterly ashamed having not leave up to your baby sister expectations.|Leave]]<</if>>
Passage Leave
<<if ndef $Toycaught>>Ana is really noisy about your failure.
<<set $AnaAffection -=10>>
<<elseif $Toycaught == "Success" >>Ana looks up to you, she's proud her sister
could do the deed and she's happy you've given her the toy.
<<set $AnaAffection +=10>>
<<else>>Ana is sad, but she tries to comfort you.
"You tried, sis, it's bad luck you couldn't catch it, that's all".
<<set $AnaAffection +=5>><</if>>
<<unset $Toycaught>>
Text about what happens next