Will You Be My Friend?

07/19/2012 12:15 pm ET | Updated Sep 18, 2012

My wife and I got married later in life, and we each brought wonderful friends to our union, many of whom we continue to socialize with today. I love going out with her lawyer buds, and the old Grisham novels and countless episodes of The Practice allow me to hold my own in many complex legal discussions. Conversely, my wife has welcomed my friends with open arms and is a real trouper through long-winded diatribes about the stock market and Longhorn football. Together, we love hearing about our friends' children's Bar/Bat Mitzvah escapades and their college choices. Yet we are clearly in different stages of life and wanted to find other friends who are interested in quality discussions about potty training, kindergarten and Disney on Ice.

Each trip to music class, Chuck E. Cheese or Toy-R-Us represents an opportunity to make that friendship that will last a lifetime. Each day we drop our oldest daughter off at school is a chance to interact with a new parent and find that one commonality that will ensure a future of family vacations and holiday parties. Since many are ten years our junior (at a minimum), we have struggled with generational disparities and have been forced to set up Facebook accounts in order to communicate with our new (hip) friends. Unfortunately, our experiences have not been without their challenges.

Early in the year, we watched excitedly as a moving truck pulled up across the street and we discovered new neighbors with two young children. My wife immediately rode over on the welcome wagon, complete with chocolate goodies, invitations to book club and suggestions for kid-friendly places in the neighborhood. We strategized about how to take the relationship to the next level without seeming too pushy. Alas, the Super Bowl seemed like the perfect setting so we invited them over for fajitas, margaritas and juice boxes. They never showed that night and waited several days to share some excuse that involved an emergency room. Despite my claims that "they just aren't that into us," we gave them the benefit of the doubt and planned a rain check evening several weeks later. We included another neighbor family that night, and I am happy to report the two couples hit it off masterfully and, from a distance, we have enjoyed watching their relationship blossom as they became very close friends.

On another occasion, my dry-witted sarcasm got me into trouble (again). I was bonding with a father of a kid in my oldest daughter's class after discovering he was an avid sports fan. During one email exchange, we were speculating about the games of the weekend, when I launched into a series of "hilarious" mean-spirited quips and inappropriate grief about his college basketball team, similar to the banter I often share with my life-long friends. I remember hitting "send" as I eagerly awaited the equally funny response in which he undoubtedly would dish it right back. Instead, the return email read simply... "Why so mean?" An explanation and apology seemed in order, if for no other reason than to ensure that his son still played with my daughter.

Finally, my youngest clearly was responsible for sabotaging a potentially lovely relationship. We were having dinner with another family when she decided she was done eating (two bites of chicken nuggets really hit the spot) and insisted on getting out of her high chair to hide under the table -- and it wasn't our table. Granted, other children (her sister) were running around this kid-friendly restaurant, so her behavior was not totally out of the norm. Still, the other family's little boy sat quietly, eating his veggies and coloring his menu. fter dinner, we suggested grabbing ice cream, but were snubbed with a seemingly ridiculous explanation about a structured schedule and getting to sleep by 7:30 p.m. sharp. For the record, at 7:30 p.m. sharp, our kids are just settling into a SpongeBob/Dora the Explorer marathon. Needless to say, we have been too embarrassed to ask for a second dinner for fear that our daughters may be perceived as bad influences.

A few months ago, we were invited to a family's home for dinner one Friday night. Since we are seldom on the receiving end of such invitations, we were initially nervous and eager to impress. We arrived only to find that the husband's parents would be joining us that evening; we were not exactly sure how to take this unexpected development. Were these people being overly-aggressive and introducing us to their folks so early in the relationship? Did they realize our advanced ages and think we would make more fitting companions for the older couple?

The night was as good a first "date" as we have ever enjoyed with another family. The conversation was easy and ventured into topics seldom reserved for such early interactions: religion, politics, constipation remedies (for kids and adults). The kiddos played well together and ran all around the house. One by one, they entered time-out for various reasons as we compared parenting (and grand-parenting) tips. The clock struck 10:00 p.m. and they showed no signs of tiring out. Finally, we chose not to overstay our welcome, shared some heartfelt goodbye hugs and handshakes and departed from this lovely evening. On the car ride home, we declared them "keepers," made tentative plans for future trips our families will take together and even joked about upcoming weddings, as their sons would make nice beaus for our daughters.

Suddenly, we re-lived the evening in our heads and worried that we may be jumping the gun. Did I say anything overly sarcastic or offensive? Was my wife being too pushy? Should my kids really have jumped on their couch? Just how long do we have to wait before calling them again? On a positive note, if this relationship doesn't work out, perhaps we can ask for his parents' Facebook info?