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Below are real letters from people just like you who are struggling to make sense of the world and failing miserably. Well, not exactly, but at least they have their health thanks to my brutal honesty and wicked sense of humor, which goes to prove that laughter really IS the best medicine.

If you have a legit problem — relationships, parenting, divorce, dating, social media drama, or finding inner peace — and would like my help, feel free to submit your anonymous request to DEAR SASSYPIEHOLE. I'll do my best to steer you in the right direction, but you might want to hold off before canceling any appointments you have with your therapist. ​
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Would You Let Pride Stand In The Way Of Friendship?

10/7/2020

 
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Dear Torn to Pieces,

Boy, do I feel your pain. While none of my friends have ever handed that responsibility over to me (probably because they were afraid of the speech I'd write), I've been invited to participate in numerous events of this nature, and cringe every time they email their registry. (It sounds worse in print).

​Here's what I am sure of: everyone is struggling, especially in today's economy. If she's smart, your friend already knows enough about you to understand whatever financial hardship you are facing —unless you haven't told her, which would lead me to question your commitment to that relationship. If there is one thing I know, it's how to be real, and doing so with her will only bring you two closer together. Your friend didn't crown you "side-queen" for a day to make you feel bad; she asked you to stand by her side on the most important day of her life because she wanted you there. That said, my advice is to take a deeeeeeep breath, swallow your pride, and call her. 

What could possibly go wrong?

It's amazing how much pressure we put on ourselves to please others, going out of our way to ditch authenticity by avoiding embarrassing truths. The funny thing is that most people, at least the ones who matter most, can give a rat's ass how much money you make or what you can do — other than being there — for them. 

Do yourself a favor: instead of bailing on your friend, pick up the phone and share your concerns with her. I'll bet anything she will make it work for both of you, even if it means skipping Vegas for a bachelorette party at a Mexican cantina.

WARNING: The following video may cause you to give up drinking forever.
Cheers, my friend. If you need a wing-man to write that speech, I'll cut you a deal.

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  • ABOUT
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