Trapped in an Endless Dating Cycle


The last post on this blog was 9 months ago! While the Lola stories haven’t stopped, the writing definitely has. Lately I’ve been getting some encouragement to “write this shit down,” since it’s so damn entertaining.

So I’m back with an update for anyone who may be interested in my never-ending dating life.

Why is it never-ending? Good question. One I’ve been trying to answer for the past year or so, when it suddenly dawned on me that I seem to gravitate towards men with commitment issues. I know the reason for this is because I too, have committment issues. Yet part of me wants to correct this “problem,” or “try again,” so to speak.

“I wasn’t ready for my first marriage,” I tell myself. “Maybe I need a “do-over” with another guy.”

But I’ve had a few opportunities to settle down in the past several years – chances to make good situations with truly good guys more permanent, yet I ALWAYS choose to run. Meanwhile, I date my committment phobic counterparts and expect them to be the one to “break” me. I don’t seem to want a relationship with someone who wants one with me, I just want it when I can’t have it. Hence, the maddening circle of endless dating.

My current situation has been the same for the past 11 or 12 years, during which time I’ve fallen head over heels in love with three different men who I can’t have and subsequently have to break it off. And when I say “can’t have,” I mean exclusively. They will take me out for lunch, breakfast, drinks and dinner, vacations, they will fuck my brains out and be a real friend, but they are unavailable to be my true life partner.  When I ask them why, the answer varies between “I’m a mess, or “I just can’t.”  I’m currently trying to end my three and-and-half year relationship with Gray, who “is a mess.”

I go with the flow as much as is humanly possible, and allow other guys a chance to win me over. I keep my heart and mind open when it comes to dating, which always makes for an interesting story.

Until next time, I’ll leave you with this anecdote about Jordan, who I met online. 

Jordan is a mid-thirties tall, dark, handsome, professional guy, just the way I like ’em. So when he messaged and asked me out for drinks, I was indeed game. We went out a few times, the first time yielding a passionate kiss as the night ended, and the next two seeming more platonic. I was going with the flow since I had told him about my current situation with Gray. I thought it only fair to let him take more of a lead. Then one night we met for drinks and pizza and I thought it would end like the past two dates, with a hug and a peck on the lips. But when he walked me to my loft, he started kissing my neck and rubbing up against my ass as I was unlocking the door.

“Oh my,” I thought to myself, somewhat delighted and very surprised. “Maybe we are finally going to unleash the beast so I can see what this guy is packing.”

We kissed hurriedly and passionately in the hallway, and as he kicked off his shoes and pushed me towards the bedroom, I was scrambling to keep up, still experiencing a whirlwind of thoughts.

We made out on the bed for a minute, and I started unbuckling his belt, anticipating the moment I would finally see his enormous cock. As he gazed down at me with lust in his eyes, I turned my attention briefly towards unbuttoning his dress shirt, and was lightly kissing his chest and stomach, all set to give that pesky belt a final tug, when he suddenly put his hand on his belt buckle and said, “Wait.”

Still in a daze, I looked up at him questioningly, as he forged ahead, “I haven’t taken a shower since this morning.”

“Ok,” I said, relatively unfazed since he works in an air-conditioned office. “Same.”

I turned my attention back to his hardness, thinking, “Now that we got that out of the way, let me at this cock.”

All at once, he rolled over and sprang out of the bed and stood over me and said, “I can’t do this. I’m sorry.”

Totally confused, and half-naked, I was trying to process and deal with the situation real-time, but he was already out of sight in the living room.  I pulled myself together and emerged from the bedroom imagining we’d discuss what had just gone down, but he was standing in the hallway with his shoes on, preparing to go.

“I just don’t want to disappoint you, if I smell,” he said. It’s nothing personal, seriously.”

I was struggling to formulate a response when just like that, he opened the door, and left!

He texted me a little later, thanking me for the date, and I kept it casual and friendly. But suffice it to say, we’re not a match. Next, please.






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