My Dad’s Friend Keeps Coming On To Me & I’m Kind Of Interested

On a scale of one to disownment, where do you think your dad would fall if he knew you were getting a little too comfortable with a good friend of his? I have an idea of how my dad would feel, but that didn’t take away the fact that I’m kind of interested in one of his friends.

He’s not as old as you think.

Yes, my dad is in his early 60s but he’s a charismatic guy and has always hung around people much younger than he is. This particular friend is about 20 years younger than him and 15 years older than me. It wouldn’t be an Anna Nicole Smith and J. Howard Marshall-type relationship, but he is considerably older.

At first, I thought he was just being really nice.

From the beginning, he was very interested in the kind of person I am—my likes and dislikes, what I do for work, what I like to do for fun. It wasn’t until we were both alone at a family function that he asked me about my relationship status. I slyly told him I was single and he proceeded to ask me to dinner. Even then I didn’t take him seriously and laughed it off as a polite gesture.

My dad would freak if he knew.

Although I’m old enough to make my own decisions about who I date, that doesn’t excuse how protective my dad is of me. Since I was young, dating has always been an extremely touchy subject, causing me to sneak around and deal with boys behind my parents’ back. Now that I’m an adult, I definitely don’t have those same issues but I’m sure it wouldn’t be wildly accepted that “daddy’s little girl” is seeing his friend.

It was pure entertainment at first, but now I’m intrigued.

I would catch him intensely staring at me whenever we were in the same room. He would find any moment to get me alone so we could talk, and he even managed to get my number out of my dad’s phone. Ballsy move! His persistent nature was an automatic turn-on and I even began to surprise myself when I started returning his text messages.

I think I’m more attracted to his security.

He’s a well-established man who’s very secure in life, and since he’s already been through the building stage we go through in our twenties, he has things figured out. He’s never been married and has one teenage child. He’s mentioned numerous times how well I’d be treated and taken care of, and although it’s intriguing, I don’t want this aspect alone to be my deciding factor.

All my friends tell me to go for it.

They think I’m crazy to not take him up on his offer and at least go to dinner. I’m not sure if its the fact that he’s older—or, more importantly, a good friend of my dad’s—but something about it feels so off. That being said, I still can’t help but be drawn in.

He makes me feel like a kid in a good way.

My smile is instant whenever he’s around. I cackle at all his jokes, and our inside ones as well. He has a way of putting me in a good mood whenever I’m feeling down and that alone makes good boyfriend material. I don’t want to get ahead of myself, but I can’t help but wonder, “What if?”

I have a feeling my mom can sense what’s going on.

She caught us talking once and although we weren’t doing anything crazy, the look she gave told me everything she was thinking. She hasn’t confronted me about it yet, but I’m sure if things were to get more serious, she would step right in. I don’t want to feel like I’m doing things behind their backs but I’m pretty sure I know how they would react in a scenario like this one.

I’m old enough to make this decision for myself.

  I’m not a child and I feel like if things would’ve been brought to the surface from the beginning, there wouldn’t be so much guilt on my end. Technically I’m free to date whoever I want. Dating a close friend of your dad’s may not be the most morally sound choice, but I’m sure it does happen.

It might happen.

 I think the fact that I’ve tiptoed around the subject for this long lets me know my stance, for now. It’s not something I’m really comfortable with at this moment and I don’t think I can get past the fact I met him based on his and my dad’s friendship. I’m a firm believer in letting things take their destined course and I’ve come to terms I should keep that same mindset for this situation as well.

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