Category: make or break relationship deadlines


July 29th, 2012 — 8:39pm

Even when you know a relationship is doomed, it isn’t easy to call it quits. I was struggling with that very dilemma during my ill-fated romance with British beau .

A milestone anniversary only brought the reality that I wasn’t in love with him into sharper focus. I now Open The Vault and take you back to the spring of 2004…

May 28, 2004

Dear Diary,
Four months ago, Riley and I went out of the first time. Sadly, this occasion only reinforces that the majority of our time together is over.

At midnight, Riley reiterated how happy he is with me—

“I still can’t believe I have such a beautiful woman in my life.”

We reminisced about our first date – which now seems so long ago. If only this could be a happy milestone for me. Instead, the more loving and tender Riley, the greater the guilt that I feel knowing he’s not the one…And it’s not hard to feel like I’m misleading him somehow by going on vacation with him. A friend, though, says cancelling the trip would seem so drastic and probably hurt even more and I think that’s true.

The weekend after we get back, Riley is going to Florida to finalize his green card approval. Somehow, I’m going to try and summon the strength to end things when he gets back. It will only get more difficult after that, because Riley’s supposed to meet the family and go to a wedding with me.

It’s so hard. Riley loves me completely and unconditionally. I wish with all of my heart I felt the same way.

* * *
I’m finally understanding how true it is that to be happy with another person, you must first be happy with yourself – and I’m not. I don’t feel settled in any area of my life other than residentially. I’m only semi employed, I’m out of shape and my organizational abilities need a major overhaul. How can I make a long-term commitment when I have so much work to do on myself?

“You make up for so many things in my life,” Riley once told me – a statement that scared me and from which he later tried to backpedal. I can’t compensate for what’s missing from his world, any more than I can expect him to do that for me.

* * *
May 31st, 2004

I find myself getting more annoyed with Riley’s quirks, and more anxious to be free of agonizing over our relationship. Every time he says something that alludes to the future, or is seeking reassaurance, I remain silent or change the subject. Because I can no longer pretend everything is okay.

* * *
Despite my emotional retreat from Riley a long-awaited trip together left me more confused – and wondering how to say goodbye.

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November 20th, 2011 — 3:31pm

It’s the dating dilemma almost everyone experiences at some point in their single life – trying to force yourself to feel something that you don’t. That’s the dilemma I faced years ago when I dated Englishman-turned-New Yorker .

After meeting at a speed dating event, Riley and I got serious pretty quickly. Between introducing me to his parents and acknowledging two months together, Riley made it clear he was ready to settle down. Having just turned thirty, I felt like I owed it to myself and him to give our relationship a chance. Still, it became harder to ignore the fact that he loved me in a way I didn’t completely reciprocate. I now Open The Vault and take you back to the spring of 1994..

April 12, 2004
New York, NY

Dear Diary,

A major milestone in my relationship with Riley last night – we said the “L” word to each other. Of course, I already knew how Riley feels – he’s shown me through his words and actions again and again.

“You’re the only girl for me. I’ve never felt closer to anyone,” he said after the big declaration. “There are no obstacles we can’t overcome.”

Part of me DOES love him. I’ve imagined saying it to him many times. But how do I know if what I feel for Riley is enough to build a future on?

* * *
April 14, 2004

For the life of me, I can’t figure out why I can’t completely let go emotionally with Riley. Dad told me the other night that I need to isolate what my doubts are and to realize that nobody is going to have 100% of what I’m looking for in a partner. I guess if I had to boil down my reservations to one thing, it’s that I don’t feel head over heels in love.

Of course, this doesn’t bode well for our relationship. But something is keeping me from walking away. It scares me that we’re nearly halfway toward my self-imposed make-or-break deadline of six months. But I’m going to hang on hope the bond between us continues.

* * *
April 19, 2004

I had hoped that being apart from Riley for a few days [for a trip to Toronto for a friend’s wedding] would make me feel weak in the knees when we reunited. Though it was wonderful to be with him again, that didn’t happen. It didn’t help that the conversation was less than scintillating – and included Riley’s exposition on the history of farting in his family. He also felt the need to share an article about a woman whose boyfriend defecates in the shower, to illustrate that it’s not so bad if Riley is occasionally flatulent himself.

I should’ve walked away from Riley when my doubts persisted after the first month. He’s told me repeatedly that his feelings for me grow stronger the longer we’re together. What in the world will I say to him when our inevitable parting comes?

* * *
April 30, 2004

Riley and I celebrated our three-month ‘anniversary’ the other day. He surprised me with a couples massage at The Plaza Hotel’s swanky spa. Afterward, while we were taking a cab down to Chelsea for dinner, I thanked him again for the pampering surprise.

“Life is too short not to splurge,” he said. “But this wasn’t exactly cheap.”

I could’ve done without that. Anyway, we went to Gascogne, a fabulous French restaurant. I couldn’t help thinking during dinner how our first date – for which we also dined Francais – seemed like a long time ago and feeling wistful for the newness and excitement of that night.

* * *
The emotional imbalance between Riley and me would soon come to a head – though it would take me another two months to confront it once and for all.

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March 19th, 2009 — 11:41pm

In every relationship, there comes a time when you decide to move forward together — or not. During my long distance romance with California native Mark (a.k.a Sparky), that juncture coincided with graduating from college.

Graduation Day at MHC: Sparky’s absence didn’t bode well for our future together

Though Sparky had mentioned (more than once) that he would fly out for the occasion, he ultimately chose not to, convincing me instead to make my second trip to L.A. in as many months.

Knowing it was make or break time for us, I packed two documents. My resume, in case I decided to stay in L.A., and a goodbye letter that I had actually started to write months before. I now Open The Vault to Volume #60 and take you back to the summer of 1995…

June 4th, 1995
Granada Hills, CA


Dear Diary,

After a long flight — with a stopover in St. Louis — I landed in L.A. with the usual butterflies in my stomach.

As soon as I entered the terminal, I spotted Sparky sitting by the gate. He stood and we melted into a wonderful hug and lingering kiss. I held onto him tightly, wanting to savor the joy and sheer delight of the moment. After 15 months, that initial, blissful high of being in his arms again hasn’t changed.

We walked hand in hand to the baggage claim, where we kissed some more.

“So, do you wanna get married?” Sparky asked. Smiling, I rolled my eyes and asked if we could postpone talking about such heavy topics until I recovered from jetlag.

“You don’t love me anymore,” he said with an exaggerated pout.

“I wouldn’t have just flown 2,990 miles if I didn’t love you,” I insisted.

In the points-for-chivalry department, Sparky opened the car door for me. As soon as I sat down, he took my face in his hands and gave me the most delicious kiss. When the Eagles ballad “Love Will Keep Us Alive” came on the radio, I told him–

“I always think of you when I hear this song.”

“Well then, let’s hear it the right way,” he said, cuing it up on a CD and raising the volume. Our hands clasped together tightly, we both sang along and said those three little words to each other.

The music continued when we got to Sparky’s house and he put on some Sinatra. I bent down and wrapped my arms around his chest, whereupon we kissed – and burst out laughing as Sparky carried me on his back while he was on all fours. Then, we danced.

“You’ve still got it,” he said, referring to how perfectly we move together.

“So do you,” I said, as we fell into another kiss.

* * *

Despite the perfection of that ‘first’ night together again, it didn’t take long for the explosive side of my chemistry with Sparky to reemerge. A road trip — and one of Sparky’s very bad habits — would end up bringing us to the point of no return.

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November 9th, 2008 — 10:10pm

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.

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November 9th, 2008 — 5:10pm

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.

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