Relationships Talk

I often (half) joke that dating is great training for entrepreneurship. Lack of predictability and control is common to both, and the discomfort of anxiety, rejection, disappointment, frustration, anger, powerlessness, and so on are inevitable. If we want to grow our businesses, we have to learn how to navigate the entrepreneurial emotional rollercoaster – and dating in 2018 is excellent practice in said proverbial emotional rollercoaster (especially in New York City).

But dating as an ambitious woman is particularly challenging – a gripe Amanda Bradford, founder and CEO of The League, knows personally. Newly single in 2014, the Stanford grad and ex-Googler was immediately frustrated with Tinder and its variations. She wanted to know more about a potential match than simply what they looked like from their best angles, and didn’t want the awkwardness of appearing in colleagues’ feeds. And fundamentally, she wanted to filter out matches who were interested in a “traditional” relationship or turned off by “Alpha” women. Aware that not knowing how to cook and being focused on her career were dealbreakers for some men, she sought to create a dating community where ambition was a quality celebrated in all genders.

After some lamenting, Bradford researched the existing apps’ founders, and realized she was “equally, if not more qualified [to start a dating app] than they were.” And so The League was born: a platform for career-driven singles that pulls data from both LinkedIn and Facebook, and keeps friends and colleagues from entering your feed.

I sat down with Bradford to download her advice for dating as an ambitious single in 2018:

Megan Bruneau: Why do you think an “equal partnership” is ideal? 

Amanda Bradford:  While equal partnerships have their own set of challenges, they’re ultimately the healthiest type of partnership as both people are choosing to be in it for reasons of compatibility rather than power or societal expectations.

That said, there’s still a stigma around being a career-driven woman, and we need to modernize our idea of what relationship looks like. He doesn’t need to be the breadwinner. She doesn’t need to raise the kids. Change is slow because many of our role models, including our parents, may have modeled a relationship different than the one I just described, but we’re getting there!

Bruneau: What do you look for in an equal partner?

Bradford: The top three traits I look for are kindness, intelligence, and humor. I’m attracted to people who want to make the world a better place, are curious, and like to learn and talk about ideas. Whether or not I agree with all of their views, I value a partner who can think for themself and have their own opinions…bonus points if they can share their views and ideas in a way that makes me laugh. When I was dating, my go-to question was: “If you had all the time and money in the world, what would you be doing right now?” You can learn a lot about someone from this question.

Bruneau: Apps have changed the dating landscape significantly. What do you see as the pros and cons of this cultural shift?

Bradford: Regarding pros, dating apps allow people to focus on compatibility. Traditionally, people dated in their immediate sphere – in school, in their neighborhood, at a bar. They didn’t have as many opportunities to meet people outside of their typical social circles. With online dating and apps, singles can expand their horizons.

There are cons, though. One of the biggest negatives of dating apps is that people treat each other more like a transaction – as if the profiles aren’t real people. Additionally, we’re so often face down in our phones looking for the ‘next best person’ that we miss out on the person right in front of us! This is why The League offers its users the ability to join local groups and events in the app as an alternative way to approach dating: it lets our users meet new people doing the things they want to be doing anyway.

Bruneau: A lot of us are afraid of dating because of fear of hurt and rejection. What’s your advice for coping with rejection and breakups? 

Bradford: I tend not to think of it as rejection – it’s just not the right fit and that person may be seeing that before you do. For the sake of self-learning, I would also try to understand the reasons the other person didn’t think it was a fit – even to the extent of calling them to inquire (warning: I’ve done this and it’s not for the thin-skinned). So many people of all genders are scared to pose this question, but this is exactly how you learn about yourself. If you approach it from a place of curiosity, it will only cause the other person to respect your emotional intelligence and maturity.

Bruneau: What are your tips for optimizing your dating profile?

Bradford: To increase sheer quantity of matches, make sure your first photo is a quality, clear, high-resolution shot of your face and body. Stay away from pictures with sunglasses, group shots, and pictures where it’s unclear whether you’re with your sister or ex-girlfriend. To reduce the number of bad first dates, be sure to express yourself as much as possible with your photos, so the matches you’re interacting with have a better idea of who you are. Photos that tend to do well invite people to ask further questions about you – places you’ve traveled, sports you’ve played, something unique and inviting of commentary.

Bruneau: Any other wisdom you want to add related to #datingin2018?

Bradford: I personally recommend you focus on doing what you love while at the same time committing to go on two dates a month. When you do choose a date, try to go out with people who are different than you – culturally, religiously, personality-wise etc. so you learn what you like and don’t like. Also don’t be so stuck on looks – they all fade! This dual-strategy gives you time to make yourself happy, gain confidence in dating, learn your true preferences, and better understand what you need in your life-partner. Then when they come along, you’re ready to poach –that’s what I did!

Finally, enjoy the process! Dating works best and leads to love when you’re having fun with it and taking chances. I flew from San Francisco down to Los Angeles for a first date once, just because I had an intuition we would hit it off…and we did! Be open-minded to people and situations that may not be exactly as you had designed them in your head – seek to learn something from each person you meet. Finally, try to stay positive alongside the (at times) sh*tshow of it all…your person is out there, I promise!