Guest & Contest: Jackie Pilossoph

Hey, Romance Readers! Want some REAL LIFE stories about romance?

In my novels, Jackpot! and Hook, Line and Sink Him, lots of stories and scenes were born out of real life situations and things that happened to me and my friends. I did that (and I do it even more in my upcoming novel, Free Gift With Purchase,) because I think it makes for really exciting, fun and colorful material. I definitely add a lot of spice and drama, just to make it that much more over the top, and to make it even more laugh out loud funny, and/or more sentimental and heartfelt.

So, with that said, I want to share a couple of my REAL LIFE dating stories that aren’t in my books. Not yet, anyway. Here is one my worst dating stories and one of my best. Obviously, the names have been changed to protect the innocent (and the guilty.)

ONE OF THE WORST : “The Visit” I met Charlie at my 20 year high-school reunion. He was cute, wealthy, and seemed like a great guy. One of my best friends talked with him for awhile and completely agreed. “How we never knew this guy in high school is weird,” she said to me, “He’s adorable!”

Anyhow, Charlie lived in Florida, and we decided we wanted to get to know each other, so he came to visit me in Chicago. I was really nervous because I didn’t want to share a bed with him since I really didn’t know him, but if someone is going to come visit you, shouldn’t you let them stay at your place?

When Charlie arrived, I told him that he would be staying in my son’s room, and he was really cool about it. The weekend started off pretty good, but almost immediately, I knew I wasn’t interested in being more than friends with Charlie. He probably knew this, since I invited my best friend, Sandy to come meet us out on our date (which was a St. Patricks Day party under a big tent next to an Irish bar in our town.) “I’ve never seen you chug beer like this!” Sandy laughed.

The rest of the weekend was painful! I wasn’t interested in Charlie, and I didn’t think he was interested in me, and we had to spend a whole day together before his flight home. It was awkward, but tolerable, because after all, he really was a sweet guy. So I thought. The day he was leaving, Charlie was showing me his new iphone and some of the cool features of it. I had never seen an iphone before. So, as it’s in my hand, Charlie gets a text that pops up in front of what I was looking at. It read, “Hi Honey, we’re out of milk. Want me to pick some up before you get home?”

I wish I was lying but I’m not. I showed Charlie that he had just gotten a text. His response: “Oh….yeah…hmm…”

I asked, “Are you living with someone?”

“Well, kind of…”

Thank God his flight was on time!

ONE OF THE BEST: “Kissing and Texting”

Anyone who gets divorced knows that when you are first going through it, your self-confidence level is as low as can be. “Who’s going to want me?” I wondered, single again at age 42. One night, I unexpectedly got the answer to that question.

My friend called me and asked what I was doing. Now, I sort of feel like the woman from “Bridges of Madison County” because my ex-husband and kids had literally walked out the door 15 minutes earlier to go to the airport for a trip, and were going to be gone for 4 days.

“Nothing,” I answered my friend, “Literally.”

She invited me to meet her and her husband “and a bunch of guys he works with” at a local bar. I figured, why not? What else was I going to do? When I walked in, I realized how young all the guys were. I got a beer and within 5 minutes, a couple of them came up to talk to me. I was hearing about some guy’s job, when I glanced over and noticed a jaw-droppingly gorgeous guy smiling at me. Within a few minutes, he walked up and introduced himself.

Fast forward-two hours and a few beers later. “I think I have to go,” I giggled.

“I’ll walk you to your car,” said Dan (Mr. Gorgeous with a really fun personality,) “I insist.”

Dan not only walked me to my car, he got into my car and began kissing me. I think we kissed in my car for three hours. Dan then asked me for my cell number and that’s when I got my first text. Ever. After the make out session, he taught me how to text! How cute is that?? He then sent me flirty texts all night, making me feel beautiful and sexy and young again. Dan and I ended up dating for about 5 months until we realized our age difference and lifestyles were just too far apart. He will always be special in that he made a devastatingly sad soon-to-be divorcee feel wanted again, and I had some of the most fun times I’ve ever had with him. We’re still good friends!

Things I love in a man:

  • A good sense of humor, someone who makes me laugh and giggle.
  • Sentimental, but not too metrosexual about it. In other words, someone who feels manly enough to say sweet things, but not a guy who spends a week planning Valentine’s Day.
  • A man who admits his mistakes and is strong enough to recognize his faults and get the help he needs.
  • Someone who makes me feel really pretty. You can tell when you look into a guy’s eyes if he really loves you. I swear by this.
  • Someone who looks good in a pair of basketball shorts.

Things that bug me big time:

  • A guy who plays the victim, who always feels like he got cheated and is angry and bitter. Quit feeling sorry for yourself and do something about it.
  • Forget my birthday? Forget you!
  • A guy whose favorite movie is Jackass!
  • A bad drunk. If you get annoying when you’ve been drinking, lose my number.
  • A bad kisser.

What do you love in a man?  And what bugs you?

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Jackie Pilossoph is the author of two novels, Jackpot! and Hook, Line and Sink Him. She also works as a freelance corporate and magazine writer, and writes two weekly columns in local newspapers. Pilossoph holds a Masters Degree in Communication from Boston University. She lives in Chicago with her family and is currently getting her third novel, Free Gift With Purchase ready for release.

If you’re interested in learning more about my novels, and reading the synopses and reviews, please visit my website:

 Contest details:

  • The prize is a download of Jackpot!
  • The contest is open to everyone over the age of 18.
  • You must answer Jackie’s question: Tell us one thing you love in a man and one thing that bugs you.
  • A valid email address needs to be included in your comment.  If you’re worried about spam, please modify your address, such as admin.bookblog AT  You can also send a message to this email after your comment has been posted.
  • While following the blog isn’t required, it is appreciated.
  • The contest ends on Sunday, March 18.

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