How do you date intentionally?

A few of my friends have asked for more details about intentional dating and how exactly it worked when I met Jason. A caveat beforehand: the approach below is what worked for me, but there are many, many ways to navigate dating successfully! Hopefully the below is helpful or maybe gives you a few new ideas to try. 

  • Being thoughtful about my goals: I know, I know, this is such an annoyingly MBA thing to do, but I found it really helpful. One of my favorite dating books - First Comes Marriage by Reva Seth - starts with the question: what is a husband for and why do you want one? I found this useful for two reasons: 1) it helped me clarify precisely what I wanted from a spouse and 2) it highlighted expectations I had about my future husband that I hadn’t realized I had. 

    On #1, I was able to articulate something that had been missing in previous relationships: I wanted someone who approached finances the same way I did. It’s made marriage much easier to know that, philosophically, Jason and I are aligned in the way we spend and save money.    

    For #2, it turned out I’d had an image in my mind that the guy I married would play the piano or sing well. It sounds ridiculous, but playing piano was a big part of my childhood (all three of us took lessons for 10+ years although I was - without question - the worst), and my family still loves musicals. Obviously, there’s no reason I needed to marry a piano-playing, musical-loving guy, and this exercise flagged that I needed to mourn my dreams of couples’ karaoke and let that preference go. 

  • Making sure my dating choices were consistent with my expectations: this sounds so basic but before I thought about my expectations, I was totally guilty of the following: I’d meet a guy who had potential to be a serious prospect, and I’d second-guess going on a date because he was “too short.” I finally implemented a dating rule for myself: I’d go on at least one date with every guy who met my list of criteria. 

  • Keeping dating expectations in check: thinking carefully about who I wanted to be with before I met the guy helped me make good dating choices, but I also had to make sure my expectations were reasonable: the goal of a first date was “do I want a second date?” not “should I marry him?” I was always terrible at letting dating unfold naturally, but I tried my best to let a relationship develop organically.  

  • Be prepared to accept: I always said I knew no one was perfect - including myself! - but it took me a while to put this into practice. Here’s a good example: I’d acknowledge qualities I wanted in a guy (e.g., ambitious, hard-working) and then become frustrated when he actually exhibited those qualities (e.g., couldn’t drop everything for a spontaneous weekend getaway). Almost every positive quality has a flip side (someone analytical can be neurotic, someone easygoing can be unreliable) and keeping this in mind helped me be more accepting.

  • Quality over quantity: dating is a numbers game (you aren’t going to meet someone if you go on 0 dates!), but even one date is a pretty significant investment of time and energy. Dating apps were the rage when I was single, and, at first, I went on tons of dates a week. It was easy to connect with a guy, exchange a few bland messages and then meet for drinks to figure out whether we’d connect. After a few weeks, though, I was completely burned out. Not only that, I’d wasted a bunch of time meeting men for drinks only to figure out in the first ten minutes that we weren’t a match (one guy, for example, was moving back home to Chicago in a month where he’d already bought a condo). To solve this, I tried to have a few phone/text/email conversations with each guy before deciding to meet in person. Qualifying my potential dates meant I went on fewer dates, but the ones I did go on were higher-quality and I’d genuinely look forward to them. 

How have you approached dating? Would you try the approach above? Let me know in the comments below!

Photo courtesy of Alok Deshpande.

Photo courtesy of Alok Deshpande.