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Single mom seeking: Mixing business with pleasure?

Why hitting on my UPS man was not a good idea

by Rachel S.  |  1676 views  |  0 comments  |        Rate this now! 

First, in my defense, he wasn't actually my UPS man anymore. He used to deliver packages to me (no, not that kind!) -- seven years ago. I will admit to ordering way too often.

Although I'd moved -- across the country -- I still fantasized about him.

We'd exchanged cell numbers way back then, in 2002, and unbelievably, we'd stayed in touch. Fine, we shared just one phone call a year. But still. That was "in touch," right?

Every year I'd visited NYC, I'd called him. He was always "busy" (in a relationship. Of course.)

But this summer, he told me that he was "free." Or, so he said.

After landing in NYC, I called him. We planned to meet for dinner later in the week. I found childcare.

I imagined some quiet, romantic corner -- white wine, tapas, candles lit. Wait, does that kind of corner even exist in Manhattan?

“The ___ Grill,” he said, and I paused.

I’d been there many times with my daughter, when we lived in New York. It’s a fast, loud, family-family restaurant. Definitely not romantic. Either he was making a subtle point -- we’re just friends, got it? -- or he wanted a hearty beef dish, served fast, because he was hungry.

I was inside the restaurant when he called to say that he was parking. So, I went outside to meet him. As he crossed the street, he was pulling on a shirt over his white undershirt. How cute was that? He was getting dressed in the crosswalk!

His first words? “When I saw you earlier, I don’t think I told you how pretty you look.”

We shared a long, sweet hug on the sidewalk. But I was nervous. It was so intense to be touching a man on whom I’d had a crush for so many years.

I did what I do whenever I’m nervous. I talked. I told him all about my never-ending crush on him.

He took it well.

“You’re making me blush,” he said.

He also added, “You sure did get a lot of deliveries!”

Then I blushed.

He was just how I remembered: a relaxed, sweet, friendly guy (he is a pro at customer service, right?)

But I was still in my reporter-mode, which I do whenever I’m restless. I asked him a string of questions -- including his relationship status. I know: I wasn't supposed to have any expectations. Still, I did not want to hurt anyone.

“No,” he laughed. “You think too much.”

Then he added, “I think it’s so cool that we’ve stayed in touch all these years. It’s really special.”

After dinner, we sat in his car and took photos, using my automatic timer. (They’re PG, but they’re private.)

About the Author

Rachel Sarah is the author of "Single Mom Seeking: Play Dates, Blind Dates, and Other Dispatches from the Dating World" and the single-mom columnist at Lifetime TV. She blogs at

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