Navigating Friendship in Midlife: A New Adventure

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At 50 years old and after nearly three decades of marriage, I find myself embarking on a new journey: seeking friendships. It may not be traditional dating, but the experience feels remarkably similar. I’m on the hunt for my new BFF—a best friend for life.

My lifelong friends, those special women I’ve known since my school days, reside across the Northeast, from Maryland to Pennsylvania to Rhode Island. These incredible ladies have supported me through every phase of life, from awkward teenage years to heartbreaks and beyond. Together, we’ve enjoyed countless adventures, from wild parties to spontaneous road trips and late-night ice cream runs. They are irreplaceable, holding the stories of my life—both the joyous and the cringe-worthy. (Trust me, there’s plenty of cringe, particularly from my ’80s perm phase.) If only we didn’t live so far apart, I’m certain we would still be gathering for drinks or catching the latest blockbuster together.

As a stay-at-home mom and homeschooler, my local friendships have come and gone over the past 18 years. Lately, they seem to be fading more than flourishing. (Cue the Friends theme song with a slight twist: “No one warned you life would be this way; your job’s a joke, finances are tight, and your social life’s MIA.”) With playdates and mommy groups now just fond memories, many of my friends have drifted away. Now that I’ve enrolled my child in public school, I find myself out of the homeschooling loop. The final blow? Transitioning back to freelancing means I can’t tap into the camaraderie of a traditional workplace. So, what’s a socially starved middle-aged woman to do?

Welcome to “The Dating Game—Friendship Edition.” No game show host is needed, but the rules remain: meet new people, ask questions, and find a connection.

Phase 1: Entering the Scene

To kick things off, I joined several local groups to explore new friendship opportunities. As an introvert, this isn’t exactly easy for me. I feel like I need a life preserver—or at least a giant pool noodle—to keep afloat in these nerve-wracking social environments. Still, I’m determined to put myself out there. I’m ready for this!

Phase 2: Building Excitement

With two busy teenagers, our family calendar is a colorful chaos of schedules. Ironically, my entries are marked in blue, which perhaps reflects the lonely state of my social life. Amidst the green and red entries for my kids’ activities, there’s just one lonely blue entry for my upcoming dentist appointment. Seriously? That’s all I have planned? I decide to remedy this by boldly adding “Mom’s Night Out” in big, bold letters. Excitement bubbles within me.

Phase 3: Getting Ready

The night of my “friend date” arrives—Bunco night, a few hours of drinks and dice that promise a lot more fun than my usual evenings spent doing laundry or playing games on my phone. As I prepare, I face the classic first-date dilemma: what to wear? I want to strike the right balance between looking age-appropriate and not entirely out of touch.

My wardrobe is divided into three categories: clothes for church and PTA meetings, outdated professional attire from the early ’90s (shoulder pads included), and casual wear. Apparently, fun and trendy items are nonexistent in my closet. I settle on some “timeless” pieces—a striped tee and forgettable pants—and head out the door.

Phase 4: Making an Entrance

Upon arriving at Bunco, I quickly scan the room. No one appears to be a serial killer, so that’s a good start. (Two glasses of wine later, everyone seems friendly, which is why pre-drink assessments are crucial.)

As the evening unfolds, I connect with many women who, like me, simply want to enjoy a night out. We share stories about our lives—career changes, divorces, health struggles—keeping the conversation light and fun. We laugh as we roll the dice and munch on appetizers.

At the end of the night, not everyone made the cut; there was the woman who didn’t laugh once (seriously, at least one of my jokes was funny!), and another who seemed weighed down by negativity. But the highlight? I walked away with two phone numbers. Looks like I’m about to go on a second round of friend-dating!

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In summary, this adventure into the realm of friendship is akin to dating—it requires courage, a sense of humor, and a willingness to put yourself out there.