One of the most agonizing situations you’ll see is when a shy friend has to start talking to another person who also is shy. They are both unsure about what to say, and hive-inducing silences can be the norm. So when you are planning to set them up to be friends or even date, take some time to understand their social challenges and prevent awkward silences.
Your shy friends are not alone. Many people find it extremely difficult to talk to other people in social situations. Your friends may be holding themselves back for many reasons. Self-criticism, self-consciousness, anxiety and perfectionism are common culprits. But shyness can also simply be how a person is wired and does not necessarily mean that anything is wrong. Due to the difficulties your friends may have starting conversations with new people, it’s no wonder you may be trying to play matchmaker. Happily, your job may not be too terribly difficult.
You may be thinking that board games are only for bored teenagers. Think again. Games have a way of opening up even the most timid folks. Maybe it’s the competition that gets people going. Or maybe it’s just plain fun. But if you host a game night and invite your two shy friends along, you can almost guarantee that they will get comfortable at some point and begin talking. So, go ahead and plan that silly game night that includes acting out scenes from movies. Your two shy friends will probably hold themselves back initially, but they won't be able to resist all the fun.
A Quiet Place Is Their Happy Place
Have you ever noticed how your shy friends gravitate toward quiet, less chaotic social scenes? Maybe they are far more likely to invite you out for coffee than to a noisy club. This is not unusual. So, can you imagine what a mistake it would be to expect your two shy friends to socialize at a noisy party? Talk about a royal blunder. So instead, find a quiet place for your friends to talk. Perhaps a local bookstore or cute coffee shop will be the perfect setting for them to chat.
Lead the Way
Once you get your shy friends in the same place, introduce them to each other and ask them open-ended questions. You can say things such as, “Mary is from New Orleans” to the guy. And then say, “How did you describe that funny experience when you went to Las Vegas and stayed at that New Orleans-themed hotel?” to Mary. This not only gets them talking, but it gives them a specific topic to discuss, which helps two shy people get over the dreaded “What do we talk about?” issue.