Brad and I had one of his colleagues over for dinner recently who got me thinking about how we found each other back in the day. He’s an intelligent, hard-working guy in his late twenties, and very mindful about his approach to dating right now. He’s hoping to meet an ambitious woman who would be a true partner in life, and he hasn’t found her just yet.
Naturally, that got me thinking about all the ambitious, badass women in our community here at Bossed Up, and how often I hear about the challenges of dating and finding the kind of guy who’s into you and your ambition. How do you go about finding one another?
But before I dive into all the lessons I’ve learned over the years that led me and Brad to finding equal partners in one another, I want to acknowledge that no relationship is perfect. And no one person has the magic answers on this kind of thing. I humbly write this with just over 1 month of marriage under our belts, and hopefully countless more happy months and years ahead of us. So while I feel incredibly grateful for the 6-year relationship Brad and I have built thus far, I know that our bond will still require tender loving care in order to thrive for years, and hopefully decades to come.
Be audacious – out loud
After our dinner conversation with his colleague, I told Brad about my plans to write this piece. I was curious what his top advice would be for women looking to attract men like him – men who want an ambitious, equal partner in life.
“Talk positively about what you want to do,” he said, “and talk about what you’re doing to get to where you want to go.”
I couldn’t agree more. Sometimes we hold our deepest dreams just a little too close to our hearts. We must give them more airtime! And yes, it’s okay to talk about your ambitions even before you know how you’ll make them a reality!
You can tell a lot about someone when you tell them that instead of hitting up happy hour every Friday night, sometimes you’re reading up on the industry you want to disrupt or heading to the gym to train for that half-marathon goal you set for yourself. Talk about what you’re doing with your time and you’ll show people what you value most.
Instead of bemoaning the aspects of your current job (if you’re not into it), or commiserating about the downsides of the daily grind, stay focused on your dreams and goals. If you talk about them and take them seriously, you’ll signal to your date that you’re looking for someone who’s down for the climb, too.
Take yourself out
If you want to meet progress-minded people, you’ve gotta spend time where those kind of people hang out! Instead of waiting to have a date take out, take yourself out, and see who else is around when you get there!
Love art? Find out what kinds of no or low-cost public events local museums or galleries host. Into literature? Hang out at poetry jams or head to bookstore events when they have visiting authors in town. Into startup culture or a particular industry? Find meetups, conferences, and industry mixers to take yourself to and see who else shows up.
Back in 2013 in Washington, DC, I was recovering from burnout by spending more time being physically active than I ever had before. For me, that meant finding volleyball circles to play in, including a pick-up league at my gym on Friday nights and just showing up at a few beach courts located on the National Mall every weekend.
I met Brad at once of those beach courts, and I’m so grateful that I’d had the courage to fly solo and just throw myself into a community full of strangers. The odds of meeting him elsewhere were extremely slim (despite the fact that we’d both gone to college in Rhode Island during the exact same time period, only a few miles apart!). In DC, our professional circles didn’t overlap AT ALL. He’d been working in architecture (a field I knew nothing about) and I’d been working in politics. Had we been like most DC-dwellers and hit the happy hour scene every day, we probably never would have crossed paths. One weekend at the courts, Brad offered to watch Teddy for a minute so I could run to the nearby port-a-potty between matches (very romantic, I know). That was all the spark that started it all.
Have the courage to show up places solo, and you might be surprised who else is around when you get there.
Don’t downplay your achievements
I’ve written before about my tendency to downplay my achievements, but it’s a story worth repeating. Brad and I were once walking down the street together, likely on our way to or from one of those volleyball matches. Earlier that day I had just had a MAJOR win for one of my clients, a Senator who I was supporting with online fundraising strategy. Without thinking much, I blurted out a major brag and exclaimed how excited I was over the huge sum of money we’d raised for their campaign.
I instantly regretted it. I thought for sure Brad would be weirded out, or think I was full of myself, or feel intimidated by my big work win. Instead, he responded with, “that’s hot.” Seriously!
In that moment, I realized something important: I’d been censoring myself around the men I liked. In my effort to not put them off, I’d been self-deprecating, coy, and subtle about my work achievements and goals. No wonder I wasn’t attracting partners who supported my ambition before – I’d been hiding it from them!
I recently stumbled upon a quote from novelist Chimamanda Ngozi Adichie on this very subject. She said, “Of course I am not worried about intimidating men. The type of man who will be intimidated by me is exactly the type of man I have no interest in.”
Follow your ambitions despite the fear
After the first 5 months of casually dating Brad, I found myself at a bit of a crossroads. This was 2013, just 3 months after I walked away from my day job to launch Bossed Up full time. Unfortunately, just 1 quarter in, I had depleted most of my savings and needed to secure a bridge job, like, STAT. While I don’t regret leaving my prior, toxic work situation before I had steady, reliable income streams established, the reality was, I needed something new to tide me over and cover my basic needs while I figured out how to make Bossed Up more financially sustainable over the long haul.
I tapped into my political networks and quickly found an opportunity to consult a political campaign on their use of email, online advertising, and online fundraising. There was only one catch: they wanted me in their offices in Portland, Oregon.
While I was really into my budding romance with Brad, I did what I had to do and left for this gig across the country. I sublet my apartment and the campaign put me up in housing in Portland. They even agreed to fly me back to DC once a month, after I negotiated hard for that perk. While I’ll admit I was a little afraid of losing touch with Brad in the process, I refused to allow that fear to stop me. I wanted to find out if he was the kind of guy who could handle me chasing my career goals and not freak out about the distance or get jealous or paranoid. And I couldn’t even give him a clear answer as to whether or when I’d be back.
Much to my surprise, there was little to no drama involved with this move. Sure, Brad missed me while I was away, but who was he to tell me what jobs to take or not take? While we had decided to date each other exclusively by this point, our relationship was still just budding. Plus, texting, FaceTime and Gchat meant we still kept in touch on the regular. I was chasing my dreams, hustling to keep Bossed Up going on nights and weekends while balancing a full-time job the rest of the week in Portland. Plus, for the one week out of each month when I was back in DC, I stayed with him! So we had plenty of time to catch up.
All in all, I spent a total of 4 months in Portland. It not only turned out to be instrumental for my career journey, and helped me replenish my savings to go all-in on Bossed Up, but it also taught me a LOT about this man. I learned that Brad was willing to walk the walk and not just talk the talk when it came to substantively supporting me and my career.
Don’t miss who’s right in front of you
I’m not a big believer in love at first sight. Rather, I believe in the power of the slow boil romance. Brad and I didn’t fall madly for each other right away. It’s more like he peaked my curiosity, and I, his. As two fiercely independent, ambitious people, we respect one another’s drive, and don’t want to clip one anothers’ wings.
What that meant in practical terms is that in the very beginning of our relationship, we would only see each other every other week or so. We weren’t exclusively dating for many months. In fact, when we first started seeing each other, I made it very clear that I “wasn’t looking for a relationship.” Smooth, right? Brad loves teasing me about that to this day.
But here’s the thing: I honestly wasn’t in a place to enter a relationship when we first met. And neither was he. Plus, I didn’t fully see all that there was to know about Brad back then. It took a long time for Brad – an introvert – to reveal himself to me. And I’m so damn grateful that for once in my life I had the patience to shut up and listen.
We’re quick to judge people. And hard-driving, assertive, decision-making women like me tend to be pretty quick to categorize suitors as either “marriage material” or not. But in doing so, we risk missing someone right in front of us. Allow yourself to be surprised. In this area of life especially, it’s fun to have your first judgment proven pleasantly wrong.
Date like a boss
Are you struggling to find a partner who loves you for who you are and supports your audacious ambitions? Do you fear putting people off by coming across as too ambitious? Why? Or are you feeling especially grateful to have found a partner who treats you like a real equal – including when it comes to supporting your career ambitions?