Dating Support from the Sidelines

As a long-time married person, it’s been ages since I’ve experienced first-hand that awkwardly sick feeling in my gut from a horrendous first date or a new relationship that is clearly not working. Dating apps have added a whole other dimension to an already complicated ritual, and I am clueless about how to navigate that. Vicariously, however, my husband and I have become adept at following the dating relationships of the many single friends and family members who are dear to us. Especially those brave souls re-entering the dating world in mid- or later life following a divorce or other major life’s change.

At the beginning of a new relationship for one of our friends, we know our role is primarily to listen, support and suspend quick judgment. Mostly we try to keep our early opinions to ourselves. But as time progresses and the nature of the relationship evolves, we sometimes find it hard to hold our views back. We’ve seen varying degrees of rotten behavior: the primadonna fiancée who broke off the engagement but didn’t want to return his grandmother’s ring to the jilted groom; the self-righteous date who ruined a charity function over a comedian’s bad joke; and let’s not forget the adoring boyfriend who suddenly confessed to sleeping with a business associate for financial gain. The list goes on.

We are protective of our friends, and we worry about their overall well-being. We don’t want to see them hurt or disappointed, and we feel absolutely awful when that happens. Conversely, of course, the opposite is also true. Imagine my joy this past Monday when my dear friend *Ann texted me a smiling pic of herself alongside her new beau. The backdrop was a clear blue sky to match the elation I could see in their faces in the photo. I had been gritting my teeth all weekend, hoping that she was having a great time, and here she was—beaming. I felt blissful on her behalf.

I had been worried because the last time Ann went away with a previous boyfriend for a winter ski trip, the weekend was unsuccessful to say the least. Her date had planned a cold-weather getaway with his friends, neglecting to mention the very tight quarters, lack of amenities and his friends’ teenage daughter who would be joining them. Before she had left for that trip, my friend had seemed to struggle with some misgivings herself—both about the trip and the guy—but she enjoyed skiing and was always up for an adventure. When she shared those feelings with me, I was unsettled by the information, and I knew it did not bode well for their weekend or their relationship. All I could do was share my concern. Ann went on that ill-fated trip, promptly ending the relationship upon her return.

As much as Ann  felt truly hurt and disappointed by that experience, she picked herself right back up and by spring was ready to re-ignite her dating app. One of Ann’s many fine attributes is her positive outlook, so when I heard about this relatively new friend she had first met in June, I wondered if he was whisking her away to meet his peeps just a little too early on. For now, it seems my worries were in vain. So far, so good, and I am thrilled that she’s happy. Nonetheless, I’ll maintain my position on the sidelines, cheering her on, but always warmed up and ready to kick some ass if the game goes south.

*Not her real name.