Category: breaking up with a boyfriend

Opening The Vault: Part Seventy Five

December 2nd, 2010 — 10:44am

When you’re dealing with the formidable foes of long distance and bad timing, sometimes love isn’t enough. I learned this painful lesson for a second time during my passionate romance back in ‘02 with Southern Illinois sweetheart Steve.

Four months after embarking on our whirlwind relationship, I found myself at a crossroads both personally and professionally. An amazing trip to Australia had me hungering to go back and live Down Under for awhile. I knew it was an opportunity I couldn’t pass up — and that it was a leap I had to take by myself. I now Open The Vault and take you back to the spring of 2002…

New York, NY
April 8, 2002

Dear Diary,

I’m feeling really sad. I keep thinking about how incredibly loving and good Steve has been to me…and it just tears me up to think about hurting him.

Over the last couple of days during his visit, there were so may sublime moments — playing piano together, singing some of our favorite songs while curled up by candlelight, kissing at the Empire State Building.

I feel more connected to Steve than I have to any man in a long time. And I will miss him terribly if I have to walk away.

* * *
April 23, 2002

I’ve taken two big steps since you last heard from me — I’ve decided to go back to Australia and I broke up with Steve.

The latter happened earlier tonight, in a brief conversation that had me fumbling for words and Steve very gracious and mature.

“I knew I’d hear those words from you sooner or later,” he said, after I told him our lives our heading in different directions.

As I struggled to explain my decision, Steve brought our final exchange to an end.

“Well, I guess that’s all I needed to hear. Have a good trip.”

I’m going to miss Steve. And I will never, ever regret a single second I’ve spent in the warmth of his arms and light of his love. Steve has shown me that throwing caution to the wind doesn’t have to be a bad thing, that the most exhilarating romances are the most unexpected ones. I love him and feel profoundly grateful he came into my life.

* * *
Little did I know when I broke up with Steve that Cupid wasn’t quite finished with the two of us. In the meantime, I turned my attention to Australia — where romance unexpectedly found me once again.

| Australia, breaking up with a boyfriend, living abroad, long-distance relationships, Opening The Vault, Southern Illinois

By The Numbers: Say Goodbye Edition

June 23rd, 2010 — 8:27pm

Like significant others, no two breakups are exactly alike. Though each brings its share of the post-split blues, what you learn that moves you forward is different every time.

As I think about how I’ve grown from my most recent split, I can’t help also thinking of the goodbye moments that have stood out for me over the years. Here are a few — By The Numbers:

Number of Breakups: 8
Number of Mutual Breakups: 2
Number of Breakups in Public Places: 3 (2 in a restaurant, 1 in Central Park)
Number of Breakups That Happened Mid-Vacation: 1
Number of Breakups Via Phone: 2

The most recent relationship-ending phone conversation, of course, was with Cleveland Chris. For once, I felt grateful to be in a long distance scenario — because I was spared the inevitably unpleasant in-person breakup scene. When someone isn’t right for you, there’s a lot to be said for parting ways in less than five minutes.

Coming up…the scoop on New York Post date #4 and a very happy hour.

| breaking up with a boyfriend, breakup scenes, By The Numbers, long-distance relationships

When Breaking Up Isn’t So Hard To Do

June 14th, 2010 — 3:26pm

When a relationship ends, it invariably marks the start of new beginning too. That’s exactly what has happened for me since I broke up with Chris.

Readers of this blog know Chris and I met in Cleveland at the start of my Great Dating Blitz. Our connection was immediate. We spent four blissful days together, reuniting in Kansas City a few weeks later and then again at the end of my whirlwind two-month journey.

During that time, we shared everything about ourselves with each other, talking a lot about the future and our mutual readiness to settle down. Sadly, a ten-day stretch together here in New York revealed some irreconcilable differences that proved too great to overcome.

Awhile back, I mentioned in a blog post that the duration of a relationship has little to do with the imprint it leaves on you. In my entire dating life, this has never been more true than it is now. Being with Chris has freed me of the two big obstacles that have been holding me back from lasting love — my late mother and my ex-boyfriend Mark (a.k.a. Sparky).

It took falling for Chris and going on my dating blitz to realize that pining away for Mom and Sparky left virtually no room for a significant other. And that, with an emotional housecleaning, should also come a physical one. Since returning from my trip, I have embarked on an Extreme Makeover: Home Edition, taking down many of Mom’s things and putting up more of my own. I feel energized with each change I make to my living space.

Yes, this time around the breakup bend feels decidedly (and happily) different. Though I’ve had a few blue moments, what I feel more than anything is at peace. Not only have I taken steps toward decluttering my life on all fronts, but I am approaching singlehood with a renewed sense of self.

As for finding Mr. Right, I’m going to start taking my own advice and get out of my comfort zone. Up next…how I plan do that, and the scoop on my first post-breakup dates.

| breaking up with a boyfriend, The Great Dating Blitz

Opening The Vault: Part Sixty Four

February 21st, 2010 — 7:09pm

Even when you’re the one initiating it, a breakup leaves you wondering how you’ll move forward without your significant other. That was never truer for me than it was back in the fall of ‘99, when I ended my relationship with noble, dashing Brit David.

My first serious boyfriend, David carried me through the painful aftermath of losing my mother to breast cancer. For a year and a half, he was my rock. As I slowly emerged from grieving, though, our personality and lifestyle differences became too difficult to overcome. I now Open The Vault and take you back to October of 1999…

October 21st, 1999
New York, NY

Dear Diary,

I broke up with David last night. And it was every bit as painful as I feared it would be.

He cried and pleaded with me to fight for our relationship. He was willing to try anything — and a part of me wanted to say yes. But I feel like we’ve past the point of being able to grow together, like all we would be doing is holding each other back.

But this is so hard! When I got home last night, David had already left a tearful message on my machine. Then, this morning, a good friend told me he had called her trying to find out if there was more to our breaking up than what I had told him. She said he was devastated — the same word other people have used to describe how David would feel if I ended things between us.

I feel so guilty. I don’t regret one second of being with him, but I feel terrible about hurting him.

There is some solace in knowing I made the right decision, the honorable decision about a man who has only treated me honorably and with unconditional love. But I can’t deny that I feel like a part of me is missing now.

I shared my whole life with David, without exception. It will take time to adjust to the fact that he is no longer the one I can share everything with. No more cuddling in the movies or kissing on street corners. No more sharing every big and small thing that happens each day.

I’m saying goodbye to a lot by letting go of David, to a way of life I never had until him. David showed me what I’ve been missing all of these years, which makes it harder to live without now.

Still, no matter how wonderful he is, I can no longer sacrifice my happiness for his. I will miss him terribly, though, and a part of me will always love him. 


* * *

It would take a very long time for me to move on from my relationship with David. A year would pass before love returned to my life. 

An editorial note — this will be the last Opening The Vault entry for awhile, as I shift gears to concentrate on The Great Dating Blitz. One week until the excitement officially begins!

| breaking up with a boyfriend, Opening The Vault, The Great Dating Blitz

Opening The Vault: Part Forty Nine

September 4th, 2009 — 8:00pm

Breaking up is hard to do, especially when it’s with someone who’s treated you like a princess. Back in ‘97, my second and final split from then-boyfriend Larry had me guilt ridden over hurting such a great guy.

A 16-year age difference proved to be too much for us to overcome, as I realized I wasn’t ready to settle down. Still, after a year together and one brief trial split, saying goodbye wasn’t easy.

I now Open The Vault and take you back to January of 1997…
January 28th, 1997
New York, NY

Dear Diary,

Larry and I broke up again the other night — and this time I think it’s for good.

Unlike our previous split (I initiated both), this separation was not the result of an impulse to retaliate for anything. When I ended things back in October, it was primarily because he had let me down when I needed him most.

Ironically, more so than he ever did before — and that’s saying a lot — Larry treated me like a princess these last couple of months. Casting off internal demons that had kept him somewhat closed off, he revealed a tender, romantic streak the likes of which I’d never seen in a man before.

Suddenly, the “little things” whose absence I’d once lamented were part of what we shared — flowers for no reason, unexpected phone calls, expressions of love.

But sadly, all of this came as I realized receiving Larry’s affections without being able to commit to him was selfish and unfair. After giving so much to our relationship, he deserves more than the emotional limbo I’ve led him into.

In an email today, Larry indicated the door is still ajar for yet another reprise between us. As much as I miss him, though, and wish I could ignore what is standing in our way, I don’t think we can reconcile.

* * *

February 7th, 1997

Larry and I emailed back and forth last week and I called him a few days ago. As always, he was full of love and understanding. He said he still wants to be my best friend, that no matter what he wants to be part of my life.

“Not a day goes by that I don’t thinking about you,” he said softly.

“I miss you,” I said.

“I miss you too,” he replied.

It was a wonderful, comforting conversation, one that made me hopeful about the possibility of us remaining in touch.

* * *
Larry and I would indeed stay connected. And my post-breakup blues about us would soon be lifted by the return of an old flame, just in time for Valentine’s Day.

| breaking up with a boyfriend, May-December romance, old flames, Opening The Vault, Valentine's Day

The Fickle Finger Of Fate

August 27th, 2009 — 1:23am

The other day, my trainer Raj told me about a few recent dating mishaps with his new love interest.

Date one ended in his parents interrupting their goodnight kiss, while date #2 found him in a brawl defending her from the advances of some brutish men. Raj’s date suggested that all of the drama was fate’s way of saying they’re not meant for each other.

As he shared this, I couldn’t help thinking about the fickle finger of fate – and the role it’s played in my own love life.

I’m a believer in signs, especially when it comes to make or break decisions about romance. Recently, I was on the fence about continuing to date hunky cop Rich, largely because of opposite schedules and (very) different emotional styles. After an intense two-hour phone conversation, he told me to sleep on it. Upon later discovering that Rich had logged into within an hour of our heart to heart, I knew for sure it was time to call it quits.

At the other end of the spectrum, I’ve experienced how the hand of fate can make romance happen against all odds. For me, there’s been no greater example of this than my ill-fated love affair with California-based Mark (a.k.a. Sparky).

A confluence of events led to our unlikely meeting back in ‘94. Knowing we were fans of “NYPD Blue,” a family friend invited us to watch the show filming in the East Village — an invite that arrived while I was home from college on spring break. I happened to visit the set just a few days before Sparky headed back to L.A., and the rest, as they say, is history.

Though neither Rich nor Sparky turned out to be Mr. Right, they both reinforced my belief that every significant other crosses your path for a reason. If you’re lucky, each partner teaches you something — whether it’s about yourself, or about what you want (and don’t want) in a partner.

That’s the thing about fate — it‘s usually a lot smarter than we give it credit for.

| breaking up with a boyfriend, East Village, fate, fate and romance,, Mr. Right For Now, NYPD Blue, online dating, spring break

Opening The Vault: Part Forty Four

August 1st, 2009 — 5:06pm

When it comes to making a decision about your future, sometimes it takes reaching in to your past to do it. That’s what happened back in 1996, as I was contemplating the fate of my relationship with then-boyfriend Larry.

A trip to Toronto, where I reunited with high school sweetheart Hogan, amplified my doubts about continuing to see Larry. I now Open The Vault and take you back to October of ‘96…

October 17, 1996, New York, NY

Dear Diary,

Larry and I broke up last night. Although my decision was a long time in coming, our final moments together were excruciating — especially because of how much I hurt him.

The man who so fiercely put his guard up months ago and who, more often than not, keeps his emotions in check, couldn’t hide the pain he was feeling. I’ve never seen the sadness that I did in his eyes, nor have I ever felt such remorse about hurting someone.

Larry is the first man who truly respected me as an equal. Despite the 16 year age difference between us, or perhaps because of it, he was sensitive enough to avoid patronizing and understanding about my insecurities.

His unconditional acceptance and affection freed me to express myself in ways I never have before. I felt safe and secure, knowing I could trust him completely and that he appreciated every part of me. If I now know the basic tenets of a good relationship, it’s because he taught them to me.

So why did I choose to leave him? Because, for all of his good intentions and honorable ways, our relationship was no longer making me happy.

Mom’s illness sharply illustrated Larry’s faults — his dark and jaded nature most especially– and that I could no longer endure them. He was incapable of giving me the support I needed. Right now, I need to be able to lean on someone who can lift me up, not bring me down.

Admittedly, Larry hasn’t had a great year. He failed the CFA, lost a friend to melanoma and recently, lost another to suicide. He couldn’t deal with my crisis compounding his own — or at least, didn’t know what to do.

I feel terrible about adding to the emotional weight he’s carrying around. I just hope he knows how sorry I am — and that I feel lucky to have had him in my life.

* * *

My breakup with Larry wasn’t the final chapter for us. Much to my great surprise, our split dovetailed with the return of a big love who continued to haunt me — Sparky.

| breaking up with a boyfriend, high school crush, old flames, Opening The Vault

Back to top