At work, I am assertive, confident, and never afraid to ask for what I want. I wouldn’t say I’m the total opposite when I go on dates, but I definitely put up with way more shit than I should.
That might be because for me, first dates feel like a very necessary chore I have to do in order to find a guy who is worth spending time with on a regular basis and who feels the same way about me. But perhaps if I approached dating with the same tenacity, self-assurance, and unabashedness that help me get ahead at work, I’d stop feeling like my time was being wasted and would have better luck — not to mention a better time.
That’s why over the course of two weeks, I decided to go on three dates and apply the rules that have helped propel my career. At least if my experiment wasn’t a total success, I’d never have to see my dates again — unlike my co-workers.
Brag about yourself, because no one else will.
I’m a journalist, and with a crazy, nonstop news cycle, my boss often misses some of the stories I publish. So anytime there’s a story I am particularly proud of and want to share, I shoot a link and a note to her — and sometimes even her boss. It’s earned me shoutouts in company-wide meetings and clout when I ask for something big, such as a raise.
On dates, however, I typically avoid talking up my successes for fear of sounding self-absorbed. But my first date with Dave was scheduled two hours after I crushed spin class and got first place on the leaderboard. So I let it slip that I was feeling extra awesome, thanks to my athletic feat. This led to us discovering a shared love of spinning, and we joked that maybe we’d have to go together sometime and see who would come out on top.
On another date, Eric, an Ivy League-educated attorney, asked me where I went college. I told him Arizona State University, which usually garners questions about ASU’s reputation as a party school. I’m always quick to defend my alma mater and my belief that you get out of college what you put into it. However this time, I needed to brag. After Eric asked me about college parties, I told him how I finished my B.A. when I was 20 and got my M.A. at 22. He was impressed and joked that I must have been some sort of child genius. I usually feel a little self-conscious telling people I zipped my way through college, but since he brought the topic up, I actually felt good not minimizing, even owning my experience.
Talk about money.
Some years ago, my work friends and I shared our salaries. Even though they had started working one year after me, I learned I was the one who was significantly underpaid. This prompted me to ask my boss to be put on a day rate like other full-time freelancers, and she made it happen. Since then, I’ve negotiated every salary and annual raise. Being unafraid to talk money has made a real difference in my paychecks, savings, and lifestyle.
For the sake of this experiment, I decided I would bring up money on my date with Nick. We met up at a cocktail bar where drinks cost $20 each, and Nick asked about my job. I told him about my career trajectory and how I feel fortunate that I am finally at a point in my career where I can afford to go out to nice places once in a while, take vacations, and even save a bit. While we were on the topic of money, I also took a moment to highlight the amazing deal I got on my one-bedroom apartment in Manhattan. At this point, I felt like I was monopolizing the conversation, so I was relieved when Nick finally cut in and mentioned how he was happy to be having a drink instead of thinking about the beating his portfolio took that day. That gave me a chance to ask him about his investment habits.
I did wonder if Nick walked away from the date thinking it was a miracle I didn’t run a credit check on him or ask about student debt or what his plans are for buying a house. But in retrospect, I suspect we spent so much time talking about money because it was the only point when the conversation seemed to flow. We had a decent time, but I’m also not surprised that we haven’t texted since.
Learn to say no.
When my plate is full at work and I am asked to take on another story with a tight deadline, I will tell my editor I can’t unless they can help lighten my workload. If I’m asked to speak on a panel after work and I’m not free or interested, I politely decline.
I’ve said no plenty of times on dates, especially when the fuckboys of the world drunkenly text to request pics or ask for me to go home with them an hour into a date. But I’ve never been good about saying no to date ideas that simply were not of interest to me, like say, dinner. (It’s my most dreaded first date next to salsa dancing.). There’s the fact that I feel obligated to see it through to the end, even when I can tell before the appetizer arrives that he’s not a good match. Then there’s the extra anxiety about him choosing a sushi spot — as they all inevitably do — and watching me awkwardly struggle to use chopsticks.
Dave, who looks like someone I’d love to stare at over many dinners in the future, suggested a fancy restaurant for our first date. In the past, I would have said yes and spent the day being anxious about the dinner, but my experiment reminded me that it’s OK to say no. I politely declined and suggested we meet for cocktails instead. He got right back to me with an alternative and seemed unfazed, at least over text. We ended up meeting at a speakeasy, and Dave never asked about my aversion to dinner on the first date. I can happily report we have since gone on a second date.
Time is money.
There’s nothing more annoying than having to sit in meetings that achieve nothing and waste precious working hours. It’s gotten to the point that I ask whether my attendance is required and if so, what is needed from me. Being firm with my time has done wonders for my productivity. I’m able to get my work done, explore new story ideas, and have a social life.
Unfortunately, I haven’t been great about applying the “time is money” concept to dating. Last month, I went on a spontaneous Sunday afternoon Tinder date with a man who my friends and I now refer to as “the irate guy who had to pee.” Long story short, he was running late, got lost, asked me where he could go to the bathroom and then text-yelled at me because apparently “walk into any business and just go to the bathroom” wasn’t specific enough advice for him. When he finally arrived, I instantly disliked him and wanted to leave. Instead, I politely sat there and chugged two pints, wasting two and a half hours — and $25 — with a man who tried to make his basic bodily functions my problem.
So before I met Eric at an alcoholic ice cream parlor in my neighborhood, I let him know that I was excited for our date, but that I needed to leave to meet my girlfriends by 8 p.m. I figured it would be easier to set the boundary for our date in advance and over text. He told me that was no problem. If he had reacted differently, perhaps trying to reschedule, I probably wouldn’t have gone out with him. It’s important to me that a guy respects my boundaries. As far as first dates go, it felt very PG, but I liked it. We talked about our favorite quirky spots in New York City and gave each other a few ideas to add to our “must visit” lists. I knew I’d either be watching the clock, or if we hit it off, I’d lose track of time, so I set an alarm for 7:45 p.m., which would be my cue to start planning my exit. Granted, I forgot how loud my alarm was, so I felt slightly awkward. Nonetheless, I’m proud of myself for protecting my time, and Eric and I agreed to get together again soon.
Ask for what you want.
No one can read my mind, so I know it’s up to me to ask for what I want at work. But I’m awful about applying this rule to my dating life, and it’s 100 percent due to a fear of rejection and not wanting to be seen as needy.
So I took it slow. At the ice cream parlor, I asked Eric if I could try a bite of his raspberry limoncello sorbet. I know it’s annoying when someone else is eyeing your food, but if a guy isn’t going to let me have a bite, well, we have a problem. When I was out with Dave, I asked if he’d go to the bar and order me another gin martini, two olives, while I was in the bathroom. He did it like it was no big deal. Typically, I’d wait for my date to offer or I’d just do it myself.
Then came the big ask. As we said goodbye, I told Dave he aced the first date and that I want to go to dinner with him. He agreed. There was no waiting around after a great date, wondering will he or won’t he text? I avoided all that anxiety by asking for what I wanted.
This dating experiment worked for my type-A personality. Dating started to feel less like a chore and more like something I could approach with a strategy for success. In the future, I will probably skip the money talk, just because I don’t think it added much value, but everything else, I’m planning to keep up. My time is precious and I shouldn’t waste it with anyone who doesn’t appreciate how awesome I am, my boundaries, or what I want out of a date.