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  • Writer's picturemildal723

Dudes and Dont's: 10 mistakes I made so you don’t have to

As I reflect on the years past, I wonder what advice I would give to my former self. On a recent trip to Boston, where many of my past mistakes took place, I took stock of some the not-so-great decisions I made in my quest for love.


Below is a collection of bad calls I made in my younger days, when fortunately, it is almost expected for you to do dumb things. I’ll admit self-esteem or lack thereof at the time played a significant role in a number of these decisions. Thankfully, it wasn’t super easy to come up with the round number of 10. Some of these are rather specific but still could be applicable:


  1. Don’t tell your high school crush that your best friend has expressed an interest in him, especially if they have no respect for “bro code” or whatever applies to girls.

  2. On a related note: Only date people that have no interest in your best friend.

  3. Don’t go to an older man’s house less than an hour after meeting him, no matter how attractive or amazing he seems to be. If you survive you may end up writing a book about your experience.

  4. Don’t secretly lose your virginity to a random person to alleviate the pressure off someone you really desire who doesn’t want to be your “first time.”

  5. Don’t resort to sex on a first date because you are not old enough to go to a bar and you don’t want to lose his interest. Not even a BJ.

  6. Never have a one night stand with your college roommate’s sibling. Despite her brother and I being consenting adults, my relationship with my friend was never the same after that.

  7. Don’t go out with someone after being wounded or rebounding from another person. especially if you are not interested in more than a friendship. It’s not fair to either of you. I spent more trying to convince myself he was good for me, when I really wasn’t feeling it.

  8. To the above point, nor should you accept being someone’s “consolation prize” or a close-second if the person they really wanted rejects them.

  9. Don’t specifically go on a husband quest because it’s the only legitimate excuse your mother will accept for “abandoning her” after her husband died. Getting married shouldn’t be your main strategy for getting out of the house.

  10. If you’re dad thinks the guy you like is a loser, he’s probably right. Mine was on more than one occasion.

What I discovered was love at first sight usually ended bad. And for someone like me with little patience, I've had far more successful relationships with people who I wasn’t totally enamored with at our initial meeting. I wish my dad was able to meet my husband (the second one anyway). Spoiler alert: I still make mistakes but I’ve been happily married for over 25 years so somewhere along the way I must have gotten it right.


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