How do you date intentionally?

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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!