Adventures in online dating…

If you’ve never done it before, online dating is a fascinating world. It’s like regular dating, but on speed. There are lots of ways to interact with people – you can send them a wink, like a photo they have posted, make them a favorite, or email them. Oh, and if someone sees that you’re online, they can start a chat session with you. The first time that happened was kind of startling.

Overall, I found people to be fairly nice and reasonably “normal.” There were a couple of notable exceptions – Like the guy who sent me a scathing email because I hadn’t responded to his wink or like of my photo (I forget which). I’m guessing that approach was not especially effective in landing him dates. Or the guy who wrote me a poem – as a first point of contact. A sweet gesture (if not a bit over the top), but the guy shouldn’t quit his day job – or perhaps he should use more than an online dating profile and a few pics as inspiration. I’m pretty sure I earned some extra time in Dating Purgatory for the amount of poem-mockery I led offline with my girlfriends. And then there was the guy who told me that I was obviously a player since I didn’t want to plan an in-person meet-up after one email exchange (as in, the exchange of 1 message). Please see note in “Diving In” re: desire not to end up stuffed in someone’s trunk (or cooler). Ironically, about 2 months later, I got another email from that guy. Apparently the rush-to-meet approach hadn’t panned out so well for him. Shocking, I know.

One of the things that was hardest for me in the world of online dating was figuring out when it felt “right” to plan for an in-person meet-up. Despite the accusations of Rush-to-Meet Guy, I was not a player and was, in fact, ready to date. But these were complete strangers, and I was aware of the capacity for things to escalate very quickly without knowing someone, well, really at all. The first guy that I took the meet-in-person plunge with was Joe. Separated-but-not-divorced, Dad of 3. Civil rights attorney. Nice guy. Funny. We had some enjoyable witty dialogue over email and text, and I figured the likelihood of being stuffed in his trunk (or cooler) was reasonably low. Despite the conventional wisdom to start with something like a coffee date, we met for dinner. We had a nice time. Good conversation, lots of laughing. But somewhere in the midst of our conversation, there were two things I noticed… First, despite self-describing as “politically moderate,” he was fairly politically conservative – on things that I was politically more liberal on and that are matters of deeply held principle for me (they are probably matters of deeply held principle for him too). Second, and perhaps more importantly, there was a rawness to the way that he talked about his not-quite-ex wife that seemed like maybe he wasn’t far enough along in the process for me. We are all works in progress (myself included), but I wasn’t looking for a fixer-upper and I also didn’t want to be someone’s “transition person.” We had a few more witty texts after that but then I kind of blew him off. I had no idea how to let someone off the hook in this world. I think I did better the next time.

After I bit the bullet and did my first in-person meet-up, it became a bit easier for me to figure out when (and whether) I wanted to meet someone in person. I went out with Kevin – military police guy, never-married but had been engaged, connected to his siblings and parents in a way that seemed healthy… But he was a bit up-tight and kept describing himself as “Type A” – which, well, (a) that’s not really a thing anymore in the land of personality research and (b) that seems like code for “I’m super up-tight” – not a selling point for me. The next day I told him that while I very much enjoyed getting to know him, I didn’t feel like we were the match I was looking for right now (Look at me taking the direct approach instead of doing the blow-off!). Then there was Steve – lobbyist, a bit shorter than he had advertised, but smart and witty and super fun. It was this 3rd first date that gave me confidence that I could do this and it would be worth it. Unfortunately, Steve was a bit more into being really casual about this, and we never had a second date – though we did exchange a few more texts and emails.

About this time, I was going to a conference, at which I would see Light Switch for the first time since our summer “romance” came to an abrupt end. Other than a couple of very formal, work-related emails, we hadn’t interacted at all for almost three months. I didn’t know until right before the conference that I was going, so I failed to let him know that I would be there. He found out by getting my out-of-office reply when he emailed me early one morning at the conference (Oops!). We ended up getting together for dinner with another colleague/mutual friend while at the conference and then he and I had a decent opportunity to talk. I felt good about the conversation and like I got something close to “closure.” When I got back home, I returned to the land of online dating. I went out with Scott – travel guy, works in nuclear non-proliferation, nice, kind of on the serious side. But I liked him. We exchanged travel stories, travel wish-lists, stories about our respective work lives… We had a good time, and he was easy to be with.

Then there was my first kind-of-bad first date. Baldy (sorry, can’t remember his name; I may have blocked it from memory) was serious. A bit socially awkward. And really hard to talk to. Conversation was like pulling teeth, and I was getting single-word, sometimes single-syllable answers even when asking open-ended questions. Don’t get me wrong, it wasn’t like a dating horror story. It was just hard. And coming off of the convo with Light Switch, I wasn’t prepared for something requiring that much effort. Baldy was also a bit pushy and clearly didn’t get that this was a boring date. At the end of the night he kissed me. I may have been thinking about Light Switch. I had to hold back tears all the way home and by the time I walked in my front door, I was practically sobbing. This was the point at which I was wondering what I was doing in the world of online dating (or dating at all) and questioned whether I was really cut out for this. But I already had another date lined up for the following week, after I got back from a trip for work. Maybe this one would go better…

3 thoughts on “Adventures in online dating…

  1. My friend Lynne, apparently a colleague of yours (who did my amazing make-up for the wedding, by the way!) sent your blog to me. We have been friends for 20 years and she has seen me through the topsy turvy road of relationships over those years. She knew your blog would resonate with me, and it did! I married the love of my life one day after my 40th birthday which included, moving out of the city for the first time in two decades, becoming a stepmom to two amazing boys (at the time 5 and 10) who we have primary custody of AND becoming a wife with a big house and five acres to care for. We met online as well and married two and a half years later.

    There are a few of us around but not many. I would love to compare notes along the way. Sadly, I was hoping to do more writing about my experiences (I’m a writer) but being a wife, full time stepmom, full time career girl, and and a commute to boot, takes up all of the minutes of my days. 🙂 A beautiful and most wonderous gift of my life.

    Keep writing… I look forward to following along-


    1. Thanks for your note! And glad you’re following along. Please feel free to chime in w your experiences and advice. And if you know others like us, feel free to send them this way. I love learning from others and also appreciate being able to commiserate w those who have been there – and lived to tell the story. 🙂


  2. Online dating is one of those things that you either love or hate. I have friends who have tried it and hate it because they feel as if they were not getting enough hits. My advice to them was to keep their profile up because it would get easier. Just like you I sometimes struggle about when I am ready to meet a guy because I feel like every situation is different.
    I enjoyed reading! I look forward to your future work.


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