The Relationship Deadline Dilemma

Not too long ago, a newly-30 friend of mine, A, told me about the impass at which she’s arrived with her twenty-something boyfriend of one year. He’s gearing up for grad school out of state, uncertain if he’s ready to settle down. She’s wondering how long to hold out for the promise of a long-term commitment.

When she said they’ve decided to see what happens in six months, I couldn’t help thinking about my own experience with make or break dating deadlines.

Having spent most of my twenties lingering in relationships well past their expiration date, I was anxious to break that bad habit as the big 3-0 loomed closer. Though I’ve had plenty of practice at saying goodbye -- having initiated 6 of the 7 major breakups I’ve been through -- I needed a better exit strategy. I latched onto one suggested to me seven years ago by my then-boyfriend.

St. Louis' Lambert International Airport: It was here back in 2001 that a new long-distance love told me his make or break theory about relationships

During an airport goodbye, he shared his simple rule about the trajectory that a relationship should follow. At six months, he said, a relationship either gets serious or it doesn’t, i.e., you end it. It seemed like the perfect one size fits all answer to the inevitable dating conundrum, should I stay or should I go?

The six-month make or break theory helped liberate me from a stifling entanglement with a clingy British guy. I said sayonara after five months. It had a much more complicated impact on my relationship with S, a canine-obsessed New Yorker I met on Match.com.

Panicking as irreconcilable differences emerged between us, I opted not to tell S my fears. I abruptly broke up with him exactly six months after we started seeing each other. Though my doubts about S ultimately proved to be well-founded, I regret bolting the way that I did. We reconciled, but our relationship was so damaged that it was never the same.

That experience made me realize how make or break deadlines, while necessary at times, can take on a life of their own. When you’re in your thirties and still single, it becomes more difficult to find that happy medium between being comfortable and drawing a line in the sand about where a relationship is heading.

As my friend A is currently asking herself, how do you know when to have that conversation and when to move on if happily ever after isn’t in the cards? It turns out there is no one size fits all answer to that question.

What I’ve learned is to pay more attention to what’s happening in a relationship now instead of fixating on an arbitrary deadline. Because it’s a lot easier to figure out what your future is when you’re fully inhabiting the journey it takes to get there.