Dating Then & Now – Molly


The first time a boy asked me out was in the sixth grade on a bus. After he asked, the popular girl next to him turned around and told me to just say no because he was asking me on a dare. Then they all laughed.

This mortifying experience began a decade of boys avoiding me and me skittishly avoiding them. I was tall and weird as heck, but I really don’t think it was the Hot Topic paraphernalia that gave me dating leprosy; it was my own internal junk and lack of self-worth.

Of course, before I had the mental maturity to realize the real problem, I just intellectualized all the reasons why boys didn’t “want” me. I concluded that since I already have this tall thing working against me, I better be skinny to cancel it out. Or if that doesn’t work, I should just get comfortable with the idea of being single forever and adopting kids. Seriously. I have plenty of frenzied journal entries about this stuff.

Finally in my twenties I began to understand how to “fix” myself:  Stop being insecure and think about my own worth and offerings instead of other people’s opinions. I tossed out the “men suck” victim card that gave power to everyone else and instead focused on myself, my projects, my friends and family, and activities that brought me joy. Once I decided to feel better about myself, I could actually start to.  It wasn’t reliant on a potential date’s opinion. I accepted my height, because being tall isn’t something to cancel out; it’s something that makes me who I am and it’s just one slice of the pie.

Once I took this time to get to know myself, then I had something meaningful to share with someone else. I viewed a potential relationship as something to add to my life, not something to define it.  


It took having a two-and-a-half-year relationship and a breakup to learn my second set of lessons. I want this kind of partner and this kind of support from him. Also, I learned that his being tall was actually irrelevant. He was totally wrong for me. I got over it in two weeks and was ready to now enjoy my single life.

Three months later, I met a 5’9” country boy in Justin boots and a Wrangler hat who was two years younger than me, and he struck up a conversation. His blue eyes, dimples, and dark Italian hair kept me listening.  I soon knew that he was hilarious, incredibly kind, loved his family, shared my values, and was confident enough to date a 6’2” girl. He asked me to be his girlfriend on the third day. Nope, not all men have commitment problems.

Then the learning process continued. I now had to really trust a partner. I knew he wasn’t going anywhere, but I still had the tendency to hide or run away at the first whiff of an issue. On the rare occasion tension came up or I felt a negative emotion, I wanted to take care of myself and not burden him. He was patient and kind while I worked through that hurdle, and now that I’ve liberated myself from it, I’m an even more confident person and better partner.

It seemed a 5’9” country boy who is two years younger than me is exactly what I needed. We’re engaged now, and we have a house together in his little hometown of 2,800 people. There’s no Starbucks here, but there is fresh air and the slowed-down, mindful lifestyle that we craved. We’re getting married in March, and the whole family is actively discussing just how tall our kids might be.

I decided what classic line I should have told that ding-a-ling in the sixth grade:  “Sorry, but it’s just not a good time. I need to focus on myself for a while.”

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