Context #1:
Brian: Why do we need to save money?
Amy: Because we need to buy a house.
Brian: But a house is so expensive.
Amy: That's why we need to save money.
Brian: How much do we need to save?
Amy: We need to save enough for a down payment.
Brian: How much is that?
Amy: That's about $30,000.
Brian: Thirty thousand dollars! That will take forever.
Amy: Not if we save every penny. Besides that, look on the bright side! We're going to buy a very nice house!
Brian: Okay, okay. Here's seven pennies.
Context #2
Maura: I don’t know what to do.
Robin: What’s the matter?
Maura: Well, I’ve been looking for a job for months everyday. I send my resume, but I just can’t get a job. I think I’m going to be unemployed all summer.
Robin: Hey, hey, hey, look on the bright side. At least while you’re not in the office, you can sit outside and enjoy that beautiful weather.
Maura: You’re right. The weather has been nice lately.
Meaning:This is an expression that means "Think positively." People use this expression when they're talking to someone who's having a problem. After saying "Look on the bright side", the speaker then says something good that the person who's having the problem can be happy about.