Question: My daughter is on a wait list at her first-choice college which, in recent years, has accepted a number of students from this list. But she has been told not to expect an update until after May 1. Meanwhile, she is supposed to make a deposit at her #2 college by May 1. Can she ask College #2 to give her an extension so that she doesn't have to confirm her enrollment there by May 1? And if she does send a deposit to College #2 and then hears that College #1 will admit her, can we get the deposit back if it's shortly after May 1?
You can certainly ask for the extension from College #2 but you will have to be honest about why you want it. And, once you are, you're unlikely to get it. Admission folks tend to be sympathetic if a student asks for an extension for medical reasons, due to a death in the family, or sometimes because a financial-aid appeal is still pending at their own school. But when it comes to getting a break so you can hear from a competitor college, you probably won't be granted any leniency. However, if you DO manage to wangle the extension, be sure to get it IN WRITING (email is fine). Don't rely on a verbal okay, whether it's on the phone or even in person.
If you end up having to put down a deposit at College #2 (likely), and then you find out right after May 1 that your daughter has been admitted to College #1, you can always try asking for your deposit to be returned. Chances that you'll succeed are pretty lousy, but if your family has high financial need, be sure to say so (repeatedly, if necessary) and it's possible you'll get your money back … especially if the good news from College #1 comes so fast that the ink is barely dry on your check.
Finally, if your daughter definitely wants to attend College #1, even after you've sent your dough to #2, make sure that the admission folks at the first school are well aware of it.