School, literally and figuratively, is back in session and it’s likely everyone is exchanging tall tales about their summer fun.

While it’s possible you are having a marvelous time hearing about X, Y, and Z’s trips to P, D, and Q it’s also possible that there’s a piece of you that is curling up inside…..from jealousy, irritation, or plain old boredom.

How can you inject some fun into these situations?

While it seems counter-intuitive, I am going to suggest that you encourage them to talk more.

Yes, it’s true.

Before you do, however, I am going to ask that you have a think about a Spanish proverb my brother learned from his favorite professor:

“Tell me your pretensions and I will tell you your insecurities.”

In other words, while your pseudo-chum may seem like (s)he is mouthing off because (s)he thinks everything about his or her life is wonderful, it’;s also possible it is being done to gain reassurance from you that his or her life is, in fact, wonderful.

And, if this is the case, this person needs your compassion.

How can you demonstrate this? By giving validation.

(Yes, I know this might be difficult at the beginning but after awhile it becomes fun.)

So if, for example, you are being told a story about how he was at the best restaurant in ‘the Hamptons’; (a phrase that gives me the creeps b/t/w; if you must refer to it at all, please call it the East End. Or, better, yet, Suffolk County) and he sent back a bottle of wine, you might say, ‘Wow, where did you learn so much about wine?”  and then let him talk some more.

In other words, these situations require a lot of ‘Tell me more about that….” or ‘And then what happened?”

What you are likely to discover is that as people become more comfortable with the idea that they have impressed you, they will be able to stop trying to impress you.

At which point, you can go from pseudo-chums to the real thing.