The answer to that question is always "No." Sometimes hearing "no" is fucking soul crushing, but sometimes somebody is just telling you that there's no cheese in your burrito or something else not so bad.
Similarly, risking a "no" from your bank teller is not the biggest deal on the planet, so just do it. What the hell am I talking about? Fees, my friend, fees.
I used to never ask for extensions on research papers. I thought, "hey, it's my fault I didn't finish this on time, I deserve to be punished." Maybe that's true (probably). But other people didn't feel this compunction at all; why would I want to be the only one being punished? So I got over it and started asking and stopped getting docked for lateness. Lesson learned.
Now I apply this lesson to my banking transactions. When we went to Canada for vacation, I shifted all my vacation funds into my secondary checking account. That way I knew what I had set aside to spend and I could track my transactions separately. After we got back I transferred back the funds. Except the hotel charge hadn't cleared completely and the exchange rate changed before it did. Which left me one dollar short and incurred a $30 fee from my bank. I just went in and asked them to waive it, and they did. No problems.
Now I imagine if I tried to do this twice a year they might not be so nice, but I've established a good history with my bank, I haven't overdrawn once (before this) in almost three years, I deserve a little clemency. And so do you :)