Gabriella – Sweet as Sugar

I matched with Gabriella on OkCupid. She’s a really cute blonde teenage girl. (I like saying that because it sounds lurid.) I’m always a little suspicious when the match seems a little too good to be true. Also, if the girl is very young. Normally that’s a red flag. But Phicklephilly isn’t going to write itself and I need content to keep it rolling. So I’m ready for anything, good or bad, to get a story out of it.

Let’s check out her profile:


19 – Philadelphia, PA

Straight, Woman, Single

My Self-Summary

My name’s Gabriella, you can call me Gabby if you’d like. I am on here because I am looking for something real and very long term. I am growing up fast and I am loving it. I live life to the fullest extent.

Some of my likes:

Art, Music, Poetry, Reading, Hanging with Friends, Being a Social Butterfly.

I would like to find a man that knows how to treat a lady. I am currently working. I am taking a year off from school to figure out what I want to do.

I have never dated an older man before, but that is my preference, mainly because I am attracted to maturity and security. No I am not after your money. I want to get to know you and I would like you to want to get to know me too.

Don’t hit me up if:

You’re a pervert, or say pick up lines, you will not get a response.

Thank you kindly.


That’s her profile. There are two cute pics of her lovely face. It’s like a pervert’s wet dream. Also…if you’re a pervert, is it something you’d readily own up to and not reach out to a pretty girl on a dating site? I can imagine the guy going, ‘Wow. She’s adorable. Looking for a sweet older gentleman to spend time with… whoops! I’m a pervert. Darn it, I can’t reach out to her now.

Anyway, unless I’ve matched with some old monster or a woman that look like an old guy in a fright wig, I’ll say hello.

But before I can do that Gabby already does this:


“Hi Gabby.”

“What’s up?”

“How are you dear. What prompted you to swipe right on my profile?”

“Just seeing what’s up I guess.”

“Would you like to meet? I know some good lunch spots or we could meet for a drink. Whatever you’re comfortable with.”

“I would like that.”

“May I have your number? Then we can figure out what times and days work best to meet up.”

“(Provides her number)

“Thank you!”

(I provide my number and create a profile for her in my list of phone contacts and add a photo. I simply call her “Gabriella OkCupid.” I text her to keep the conversation going.

“Hi Gabby. What days and times are you free?”

“I’m not to sure yet lol. Probably next weekend.”

“No worries.”

“What did you have in mind?”

“Well it’s a Saturday, I was thinking we could stroll the art museum and get to know one another. Then get a bite to eat if you wanted.”

“That would be neat. I’d like that. Where are you from by the way?”

“I live in Rittenhouse. You?”

“King of Prussia.”

“Ok. Not too far.”

“What do you do for fun?”

“Hang with friends, write, explore the city, enjoy the arts.”

“Nice! I like those things too. I’d like to travel and see the world one day.”

“Travel is great. It’s so broadening to learn that the world is a bigger package than most can perceive.”

“Yes. I’d like to travel somewhere interesting like India.”

“India would be amazing. I’ve never been, but I know several people who have and they said it was quite the experience.”


“In your profile you said you were taking some time off from school. What is your course of study?”

“Marketing currently.”

“Cool. I have a friend who just got a good position with a marketing company. Are you working in marketing now to get more experience?”

“I’m a waitress now. Does your friend need an intern?”

“Noble work and not easy to do. I’ll ask her!”

“That would be sweet!”

“I’ll do what I can. I have lots of contacts in the city.”

“Nice haha That’s always good.”

“What are you up to today. Working?”

“Yeah I got work later. Sucks. I wish we could have hung out today. But next Saturday I’m free all day and all night.”

“Life is what it is. Let’s shoot for museum day next Saturday, Gabby!”

“And after?”

“I guess we could get some food and drinks if you’d like.”

“Wooohooooo!! Haha”

It’ll be fun. I’m looking forward to meeting you.”

Yes. You too.


The conversation ends there. So if you see another entry in the next week or so you’ll know that we either spoke again and it fell through, or we went to the museum and it was on.

I am actually hoping that we go out. If she’s the real deal and goes through with it today. I love getting all of the looks from women my age. That scorn in their eyes. Me out with the little tart. I’m a cradle robber and a dirty old man. It’s so fun.

Even if in the rare case that she’s legit, I’d be happy just to hang out with her on occasion like I do with little Emily. (See: Emily 2016 to Present – Pretend Sugar Baby) As much as I come off like I’m the Dark Lord, it’s all just an act. I’m a nice guy who’s a dad and respects and loves all women. I’d be happy to be a mentor to her if nothing else. There’s enough bad guys in the world. I may be fickle, but I’m for real.

Until next time!


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Author: phicklephilly

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8 thoughts on “Gabriella – Sweet as Sugar”

  1. Be careful, it could be a catfish.

    Then again, I’m someone who prefers older men. I got annoyed at a friend of mine recently who questioned it and said older men were creepy. If anything, guys my age and younger are creepier.

  2. Interesting. Who am I to object? My experience with older men has always been disappointing, they tend to be controlling and I don’t like that, so I dated much younger men and am currently married to one. The downside is that in general they lack some of the finesse older men may have but the upside is that I don’t have to worry that they are going to inhibit my creative side or my desire to do my own thing. There’s nothing worse, than someone telling me I should or shouldn’t do what I want, especially if I’m paying the tab. My younger man however is maturing now and starting to become more and more possessive as time goes on, like “you’re going to do that without me?” (Gag me). Is it time for me to move on maybe? (smile) Enjoy!

  3. I am still catching up on my blog reading since my return to Australia, hoping there is part 2 in my email somewhere!! It sure is motivating me to catch up a little faster 😛

    1. In the near future you’ll start to notice that if any post has a Part 2 or 3. It will be published the next day. I’ve just found that it keeps the continuity to the story.

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