Most of us instinctively close those annoying pop-ups that ask if we'd like to be pestered by a "live sales representative" when we're shopping online. However, that may actually be a great time to ask for a discount.
As finance blog Three Thrift Guys points out, most live chat salespeople have the same goal that regular sales people do: to sell you things. This can be annoying, but it also means that you can solicit them for deals or discounts:
Next time you are shopping online, look to see if a store has a "Live Chat" function. If there is one to be found, you'll usually find a link to activate it in the customer support section of the site. Stores advertise these chat specialists as experts there to help you make a decision, but they are really just salespeople in disguise. Use it to your advantage and make them sell you what you came to buy -- for less.
This won't always be successful, and sometimes the person you're chatting with may be working off of a script (or they could be a robot). However, the goal is still to make a sale. Any time a company puts a person in front of you whose motivation is selling, that's an opportunity to haggle, and it's worth a try. Check out Three Thrifty Guys' post for more ways to save money while shopping online.
5 Ways to Score a Deal Without Leaving a Store's Site [Three Thrifty Guys]