Welcome to FT!

I'd recommend that you peruse this thread, and the Wiki at the top of it in particular, for some relevant information and advice:

http://www.flyertalk.com/forum/infor...uddy-pass.html

Where are you traveling from and to? And on what airline? The specifics can make a difference in the likelihood of having any problems (e.g., is it a popular route during, are there lots of flights on your airline for that route each day, are there other airports in the region you could use as an alternate, etc, etc)

But in the end no one can really say for sure that you will or will not make it on your desired flight and desired day. You're planning to come back the day before you have to be back to work. However it's entirely possible you might not get onto a flight home that day...or the next day...or the day after...etc.

If you absolutely cannot miss work the next day or two, using this buddy pass may not be the right option for you with this itinerary. Or you would need to be prepared to purchase a very expensive last-minute flight home as a last resort.