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Thank you for your feedback on this one! I have thoroughly enjoyed hearing your horror stories. Below are 10 “IShouldveKnownWhens sent in by YOU!

1. Less than 20 min. into the first date, he asked me to train with him for a 1/2 marathon and wouldn’t take no for an answer.

2. He said he often forgets to eat breakfast. And lunch. Oh, and dinner, too. Huh??

3. He shared a bedroom with his sister.

4. He showed up to our date on rollerblades

5. I found out he was born in the 90’s.

6. Sent me a shirtless selfie.

7. Takes shirtless selflies.

8. Said he couldn’t drive at night b/c saltwater and sunlight had ruined his eyes

9. He told his friends we were together after our third date.

10. LOVED vikings. And told me about it.

Send your stories over:) Or use the hashtag #IShouldveKownWhen



Photo by We Heart It




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00991ef96cbedfc9d0f4abdf6d8bcad5Thanks for the positive feedback on the Red Flags!  I know this is directly after a R.F. post, but I am sitting here with my roommate Melody and we can’t wait to roll out another platform for your enjoyment (and hopefully participation).  The credit for the hashtag #Ishouldveknownwhen goes to Melody.  We use it around our circle to describe the moment you realize it’s not going to work out with someone. (Unfortunately, all of us have ignored it a time or two) I’ve had several friends send me their #Ishouldveknownwhens and here are the first ten.


  1. He asked me to drive an hour to our first date
  2. He wore more jewelry than me
  3. He wouldn’t sign-up for a trial gym membership because three months was, “too much commitment”
  4. Thanks to Google I discovered he is famous in the gay blogging community as an underwear model
  5. He introduced me to his cats. Plural.
  6. At dinner he referred to me as his “sister-in-Christ”
  7. He has a girl best friend
  8. After our first date he invited me to Thanksgiving
  9. He had more Instagram selfies than a fourteen-year-old girl
  10. He said he had a special Italian spot in mind for our first date and then dropped a pin at the Olive Garden


And so the girls don’t have all the fun, one of my favorite #IShouldveKnownWhen came from my guy friend: He should’ve known when she said,  “Don’t worry about all the arm scratches, they are from my bunnies.”

Now it’s your turn! #IShouldveKnownWhen anywhere you like to hash or email me:)