Dating FAILS

Come share your worst dating stories with us!

Is It Really The Thought That Counts?

Tell me the worst gift you have ever received from a significant other. Mine comes from a high school boyfriend and has yet to be topped.

His Dad had passed away when he was younger and while we were dating he went to the cemetery to visit. I was happy to see him later that day especially when I saw he had a tall box in his arms which I knew just had to be long stemmed roses. And they were! Only they were of the fake variety. You know…. the kind you would buy for a gravestone. Yes, that’s right, I received flowers from a cemetery.

In the interest of diversity…

With the recent ruling in NYC allowing same-sex couples the right to legally wed, I think it only right that we here at Dear (Ass)Jack also extend the spirit of openness and inclusion to those living alternative lifestyles.

Therefore, I would like to invite any ladies out there with a Dear Jill story of heartbreak, relationship woes or dating hell to feel free to share it here… in great detail… seriously, let it all out sisters… with pictures if you have them. And to be fair I suppose guys can post a Dear Jack letter too if they wanna. But I'll let Sassypants read those.

Hey, I was invited to contribute here to offer my perspective on things as a guy. Well that's pretty much it right there.

Dating

Dear Jack,

When you post on a dating site saying you are looking to  "Date"  I assume that is what you are looking for.  But after many emails back and forth you tell me, "Oh I should be honest I am only looking for a friend. I have a girlfriend."  What?
Then proceed to tell me after a few more emails that you and your girlfriend want a 3some and don't want it with a total stranger so you are using the dating site to meet someone so they aren't a total stranger really?
Then ask me if we can still be "friends".  Also must note you weren't my top pick by any means!  So the fact that I lowered my standards and this is what I came out with?  Shame on me!  What kind of people are really out there?   Any normal ones or am I just asking for too much?  I will go back to the 50 something year old guys and the 20 something year olds that are looking for "cougars". At least they were honest.

Chalk Tease:

Dear Jill,

Thanks for letting me spend an entire school year longing for you when you knew from the start that you were never going to give me a shot. All the time I spent thinking about you, all the bad poetry I wrote for you, all the little gifts I snuck onto your desk when I thought you weren't looking, all for nothing. So what if you were 32 and I was 12 at the time? You could have been honest with me instead of leading me on, stringing me along all the way through the 6th grade. And to think, I clapped your erasers for you. I was such a sap.

Really?????

Dear Jack,

I loved how we chatted through email and texting for weeks and I was looking forward to finally meeting you. We met and had a great time chatting for 4 hours at the restaurant, laughing and enjoying each others' company.  Only for you to never call me again? Really?? I did enjoy that HUGE waste of time!  Too bad for you too.  You were really hawt! Now? Not so much!

Sincerely,

Sassypants

Tell Us About It!

Dear Friends,

Here's the place for you to share your letters with us. Please post a comment and tell us about the special assjack in your life.

Yours truly

Sample Letter

Dear Jack,

Thanks for stringing me along for three long years with the promise of a future life together and then leaving me for my hair stylist Felipe!  Do you know how long it took me to find a good stylist??? Assjack.

Yours truly

What We're All About

Let me start right off by saying that this blog is NOT about bashing all men. We love you guys! It’s how we got our hearts broken in the first place. Men are always welcome here. This blog is to specifically address the one or two assjacks we’ve encountered in our lives who left us heartbroken. 

It’s about gaining closure through writing a letter to “Jack" OR to "Jill." The assjack gene does not discriminate based on gender. We can tell him or her what we never had the chance to say at the time of the break-up.

It doesn't even have to be a recent break-up. You may be happy and in a healthy relationship right now. But that little prick from middle school who broke your twelve year old heart still pops up in your mind from time to time. And yes it’s thirty years later but you still think he’s a little prick. Whether he is or not is irrelevant. You’ve been carrying around this negativity for thirty years!!

It is time to purge those feelings in a healthy way. So go ahead and write down everything you weren't able to say then. Write without restraint knowing  we support you…. write knowing that we empathize with you.

Bashing other users will not be tolerated on this site. All rude comments will be deleted and ten years of bad relationship karma will befall the poster for annoying us. I can’t explain exactly how that part will work. It’s all very scientific so you’re just going to have to trust me on this one. Be kind to one another. Lift one another up. Remember you know just how they feel.