Watch Your Mouth

"It'll be tough to start over at your age."

While you may be trying to come across as understanding, this statement sounds like you think your friend has missed her moment and that no one wants to date an "old" divorcee like her. What's likely going on is that you're worried for your friend—and possibly yourself, too. People tend to impose their own fears on outside situations: What if it were me having to start all over again? But the last thing you want to do is be a downer or to invoke panic in your friend, says Reynolds. There is a way to express your concerns tactfully—but only if she brings up the topic herself, says Reynolds. "You can say, It might be tough, but if you want to find a new relationship, I know you can."