Friendship Challenge: Unexpected Success

Since this is Friendship Challenge week, and I’m really hoping people will take take on this mission and share their “ask her out” experiences, I thought I’d try to inspire you with a tale of one of my most embarrassing–but most rewarding–pick ups.

I was at dinner at a nearby restaurant with Matt (happy 30th birthday Matt!!), and two friends from out of town. We had the greatest waitress. She was spunky. She made us laugh, but without trying too hard. She seemed like absolute BFF material.

“She’s cute. She should be my BFF,” I said.

“Ask her out,” Matt said. “Leave a note.”

I knew it was a great suggestion–I’d been trying to test drive new ways of meeting people–but just the thought made me nervous. What if she thought I was crazy? Or trying to really pick her up? What if she thought I was a desperate pathetic social leper and I got too humiliated to ever return to that restaurant? It was our favorite!

After a meal full of pep talks, I decided to go for it. But, just in case it was a total disaster, I made my friend write the note for me. She had better handwriting anyway, and if our waitress saw the whole thing go down and decided the writer of the note was a nutcase, at least I could still eat dinner there. Jenny, my dinner companion, was from out of town so she didn’t stand to lose those delicious scallops.

And so Jenny wrote a note, dictated by me:

“Hi! I’m new(ish) in town and I live around the corner with my husband. You seem cool  and like we could be friends. Would you like to get lunch sometime? Let me know!”

For a four sentence email, let me tell you it took a lot of thought. Jenny wrote the note on the back of our receipt, and I was pretty confident I’d never hear from the waitress. She might not even turn the receipt over!

Except she did. And she wrote me back that night. And we went to lunch. And then to drinks. And then she gave me free food the next couples times I stopped into the restaurant.


The point of this story, of course, is that you never know. I thought leaving a note on a restaurant bill was a no-chance method. But I was wrong.

If you’re holding back, you could be surprised too.

What’s the craziest route you ever took to meet a potential friend? Anything totally unexpected? And did this story make you say, “Yes! Today I will totally ask that PBFF out to lunch”? Anybody? Bueller?


Filed under The Search

3 responses to “Friendship Challenge: Unexpected Success

  1. Taylor


    I’ve been following your blog for a few months now. I moved to Dallas from Denver in June because my long term boyfriend had a job here and is in grad school and I got a job here and we were both very tired of doing the long distance thing. I’ve always been a “BFF” type of girls, most of my current friends are friends that I’ve known since elementary school or even longer. I think I found your blog by googling “how to make friends in a new city” or something similar. I subscribed and have been reading every post since.

    This blog has been such an encouragement to me and has really motivated me to branch out and try to meet people. I guess before all this, I never really thought anyone else was in the same position as me, but the more I look around, the more I realize this is a HUGE issue with women in their 20’s and 30’s.

    My most recent friendship move was last week. My freshman year in college, I had a really bad potluck roommate experience. I toughed it out for a semester and then switched as soon as I possibly could. My roommate’s best friend who I remember thinking “I dont get it. How can such a nice normal person be friends with this mean and messy person?” I spoke to this girl a time or two when she would come over to our dorm room, we became facebook friends, and never really saw each other throughout our years at college. Fast forward, five years later, I see that this friend of my freshman roommate has moved to the Dallas area. She posted a status about how she needs to make friends, because she’s bored out of her mind. I message her on facebook, before I can talk myself out of it, and tell her I am only a few minutes away from where she is living and would love to get together for dinner or drinks.

    A couple days later, we’re sharing fajitas and drinking margaritas, totally hitting it off. This weekend she came over for a football game watching party with my boyfriend and all his guy friends. I’m not saying that we’re bff’s yet, or even will be eventually, but it sure is nice to have another girl around. Funny though, it turns out, she tried to live with my old roommate the following year in college, and things didn’t work out so well.

    Anyway, I just want to thank you again for being brave enough to blog about all this and for being such an inspiration to me and many others..I will definitely be buying your book. Congratulations on all your successes!

    • Hi Taylor! Thanks for sharing this story. It sounds very promising in terms of this new girl!

      I’m so glad you ate enjoying the blog, and your kind words made my day. Keep us posted on how it goes! And just remember you are not alone, so many of us have been there. Dallas will turn out great!

  2. Pingback: She’s Out Of My League | MWF Seeking BFF

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