Who's the most inappropriate person you ever dated?

nomadica

When I was 21, I dated a 42 year old man for about a year. Yup, twice my age! My friends were sooo unsupportive, but my family was surprisingly ok with it (I guess they figured since I never got in trouble and had always done well in school, I coud make reasonable decisions). Anyway, although he was definitely immature for his age (never married, lived with a roomate, no financial managemen skills and zero money), he was extremely smart and funny, very political, and treated me like a queen. He was my first real love, actually. We reluctantly ended the relationship after a year because I think we both knew we didn't have a future, but I'm really glad I spent that time with him.

P.S. The guy I dated after that was also older (30) and going through a divorce, and one of my friends said, "What's next, a priest?!":)

You?

danto

The VP of the company I worked at.

lilbit923

I dated a man twice my age who was also a police officer but worked in a different state. It was extremely short lived but I loved the attention at the time.

Happy2beMrsT

Fun game! Mine would be a guy about 10 years older than me...I was 22 at the time. We had NOTHING in common and I knew it was going nowhere, but he was super hot and let's just say that he was very talented in bed.   It made my family insane! He was a sweet guy and treated me well, until I broke it off with him and he turned out to be a little bit of a stalker....

nikll34

One of my old high school teachers... well technically I never had him as a teacher. He is 10 years older than me, but he is very, very cute. We have a ton in common and he is extremely funny. However, he doesn't want to settle down and still needs to grow up a little.

greengirl0909

Egads...do I only get to pick one? I've dated someone 20 years older, 5 years younger, and my boss.  All of them leading me to the conclusion: THANK GOD FOR DH!!

laurieb602

My daughters father...yikes.

He was the typical bad a$$, I was the straight A student...to this day I have no idea what attracted me to him (may he rest in peace)

spring_time

A guy who was 10 years older than me that I met in a bar.  I was on the rebound from a long relationship and was looking for a good time.  He was completely unreliable and irresponsible, but he was fun.  He spoiled me and always knew about the fun events in the city.  He was incredibly spontaneous, which was sometimes good, but sometimes left me stood up.  Sometimes I miss the spontaneity and wildness because DH is very cautious and nervous about going into the city (it really isn't so safe unless you know where to go - Detroit), but then I remember the lies and his completely unreliable nature.  His life was one big party and I couldn't sustain that for any period of time.

My other one would be my boss' son.  He was also older and completely unreliable, however he was beyond gorgeous.  He was my first love, but looking back I realize that he really treated me like crap.  At one point he took me on a date to the movies, but spent the time watching his portable television he brought in his pocket (this was 14 years ago, way before smartphones and such).  After that relationship, I learned how NOT to be treated. 

monj76

 I am not proud of this, but I dated a married man. He was separated from his wife, but she was pregnant with their second child. He was with me for almost 6 months, and went back to her right before the baby arrived. I did still see him a couple times after they got back together, and that is why I am so ashamed of it.

 I got what was coming to me though, because my DS1's dad was cheating on me the whole 3 years we were together.

monj76

nikll34:

One of my old high school teachers... well technically I never had him as a teacher. He is 10 years older than me, but he is very, very cute. We have a ton in common and he is extremely funny. However, he doesn't want to settle down and still needs to grow up a little.

Present tense? Is this recent?

monj76

Also I dated a 24 yr old when I was 17, he was really gross now that I look back on it.

lilbit923

monj76:

 I am not proud of this, but I dated a married man. He was separated from his wife, but she was pregnant with their second child. He was with me for almost 6 months, and went back to her right before the baby arrived. I did still see him a couple times after they got back together, and that is why I am so ashamed of it.

 I got what was coming to me though, because my DS1's dad was cheating on me the whole 3 years we were together.

I am not proud but dated a married man once too. I believed all the lies..."I'm gonna leave her" blah blah blah. I regret the relationship and am also ashamed of what I did. When I started dating DH, he asked if what bad things I had done in my life...trying to get to know each other. I told him about the married guy, why I did it, why I regret it and what I learned from it. I didn't want to start dating someone new and have it start with lies like I never did anything wrong. I know I am flawed and wanted to be honest about it.

nikll34

monj76:

nikll34:

One of my old high school teachers... well technically I never had him as a teacher. He is 10 years older than me, but he is very, very cute. We have a ton in common and he is extremely funny. However, he doesn't want to settle down and still needs to grow up a little.

Present tense? Is this recent?

 

No, sorry. He didn't want to settle and he still doesn't. I still talk to him and hangout with him though. H knows and is fine with it. We are really good friends and we all get along well.

 

ETA: He has a girl friend right now and he cheats on her all the time. That poor girl has no idea and she is so sweet. It's hard to decide if I tell her or not, but I'm not really close with her so I feel like it's not my business.

mrs.vanderwall

When I was 17 I dated a 24 year old.  He was really immature for his age, but it was still quite inappropriate being in High School and all.

emily0829

M sophomore year of college I dated my Sociology professor. He wasn't THAT much older than me, but still inappropriate nonetheless.

GreenNGold

I dated a dad of one of the babies in the infant room I worked in. He was divorced, but 10 years older than me. It was fun whie it lasted.

monj76

nikll34:

monj76:

nikll34:

One of my old high school teachers... well technically I never had him as a teacher. He is 10 years older than me, but he is very, very cute. We have a ton in common and he is extremely funny. However, he doesn't want to settle down and still needs to grow up a little.

Present tense? Is this recent?

 

No, sorry. He didn't want to settle and he still doesn't. I still talk to him and hangout with him though. H knows and is fine with it. We are really good friends and we all get along well.

 

ETA: He has a girl friend right now and he cheats on her all the time. That poor girl has no idea and she is so sweet. It's hard to decide if I tell her or not, but I'm not really close with her so I feel like it's not my business.

Got it. I was gonna say, wow talk about inappropriate!

nikll34

monj76:

nikll34:

monj76:

nikll34:

One of my old high school teachers... well technically I never had him as a teacher. He is 10 years older than me, but he is very, very cute. We have a ton in common and he is extremely funny. However, he doesn't want to settle down and still needs to grow up a little.

Present tense? Is this recent?

 

No, sorry. He didn't want to settle and he still doesn't. I still talk to him and hangout with him though. H knows and is fine with it. We are really good friends and we all get along well.

 

ETA: He has a girl friend right now and he cheats on her all the time. That poor girl has no idea and she is so sweet. It's hard to decide if I tell her or not, but I'm not really close with her so I feel like it's not my business.

Got it. I was gonna say, wow talk about inappropriate!

 

haha yes, I think that would have taken the cake. 

DaisyFull

Oh, fun! Let's see... when I was 20, I dated a 36 year old, who was also the son of the owner of the company I worked for. He was very well off, and it was FUN. He taught me how to sail, how to water ski.. he took me on lots of trips and spoiled me rotten. He never wanted to settle down though and lord knows we weren't really going to make a go of it when I was 20, lol.??