How do you get two friends to date each other?

Don't be afraid to pair your friend up with a younger man. Be clear about how you know him. Interfer only if there is confusion after the first date. The best way to bring them together in the same room, Spira says, is to host a dinner party.

It takes the pressure off both of you, and if things get weird or you don't really get along, there are other people to talk to. When transitioning from friends to dating, being open and honest is paramount. Direct communication is the key to any relationship, according to Dr. Sterling, but the transition from a better friendship to a romantic relationship is a minefield.

The best way to navigate this uncharted territory is to be direct from the start. That means clarifying what type of relationship you're going to have. Is this a friends with benefits situation or are you looking for a long-term relationship? It's important to answer these questions early on so that both of you can move forward carefully. Talk to both people and make sure there's no jealousy involved, or choose to form friends who don't have exes in the inner circle.

Here, psychotherapist and relationship coach Toni Coleman gives you two cents for playing matchmaker, and how not to ruin your friendships by throwing them down a drain of ~undestined love~. If you think that 2 of your best friends would make a great couple, you can try setting them up for an informal meeting.