18 First Dates

After dating two women back to back for a total of 5 years, I needed a break. I was intentionally single for about 5 months (for the most part), and I stayed single for a while after that. But I wanted to be more open to meeting women again, and I felt that my heart was ready to meet someone special. I had never tried online dating and wanted to give it a go, so I signed up for a three-month subscription on Match.com and a free membership to OkCupid.

Here I am, three months later, my Match subscription about to end, and I’m still technically single. I’ve met a lot of great women, and I’m honored they’d go out with me, even just for a date.

Why stop now?  To be honest, I’m exhausted. I’m not saying I’m giving up on dating, not by any means, but on Match, there’s a constant influx of women. You wink at one woman and three wink back. I don’t want that to be my dating life forever. In small doses it’s fine, but I can’t sustain this.

And in a way, my willingness to meet new women during these three months hasn’t been completely fair to the women themselves. By entering a world of thousands of options, I made it difficult for myself to give my undivided attention to any one person. In hindsight, I wish I had limited my subscription to a single month and just renewed it a few times–three months is a lot of women to talk to, while one month isn’t as many.

18 first dates (and many other dates) in three months is also expensive! After the first girl I went out with ordered five glasses of premium wine over dinner, I decided to avoid first-date dinner dates in the future. For the most part, most of the first dates were over a beer or two, as well as a few root beer floats (any woman who wants a root beer float on the first date is my kind of woman).

I learned a lot about myself by going on these dates, and even more about women. I need to add a few questions to my “perfect woman” survey:

  1. I’ve found that arrogance is really unattractive (the “it’s his loss” attitude…please, women, I know you feel empowered when you say that, but that’s for your best friend to say about you, not you)
  2. Trying too hard to be cool is unattractive.
  3. I’m a little hesitant if you have a dog.
  4. If you’re still into going to nightclubs, that’s cool, but we’re in really different stages of our lives.
  5. If you ever stop talking and say, “Well, enough about me,” you’ve actually reached the point of conversational imbalance well before you stopped talking. Here’s the lesson, and it really isn’t that hard: Ask questions. Force yourself to do this even if it doesn’t come naturally to you.

I’ve also learned a few things about online dating:

  1. It’s okay to ignore people. I know, this sounds odd and perhaps offensive, but I’m telling you, ignoring an e-mail or wink from someone is way better than creating the awkward situation of replying and then revealing a few e-mails later that you’re not at all interested. I realized this was okay when I started to notice that I couldn’t remember the women I had winked at who hadn’t replied. Even though I might have been excited about them when I winked at them, a few days later, I had no recollection of it if they hadn’t winked back. I think there’s only one woman I winked at and e-mailed who I was genuinely disappointed that she hadn’t replied (her profile indicated that she reads Fast Company magazine, which is just hot for someone like me who’s always thinking about business ideas and structure).
  2. Don’t say in your profile that you “love to have fun.” “Fun” is inherently something good. It’s not something to like or love. It’s not like some people like fun and other people love fun. Please, show me someone who doesn’t enjoy fun. And while you’re at it, start thinking of real, actual things that you think are fun and put them in your profile instead of that generic, meaningless phrase. (Yes, Match has made a cynic of me.)
  3. Don’t suggest we meet up in your first e-mail. That’s way too fast, and it’s creepy. You don’t even know me and you want to meet? Let’s e-mail for a bit and see if we’re on the same wavelength first.

One of the big takeaways that I have from this whole experience is that it’s okay to live in the moment. Even though I got on Match looking for someone special, a first date isn’t necessarily a gateway to marriage. I was reminded of this by one girl who had a dog. On our second date, I expressed my concern to her about Biddy meeting her dog (and being attacked by her dog). She said, “Why does Biddy have to meet my dog?”

And she was right. It was our second date. I didn’t need to worry myself with future logistical concerns. If those are valid concerns, they’ll come to the surface soon enough. But I should just enjoy the second date.

You may be wondering how many second dates I went on. I estimate about seven overall. I’m not sure if that’s high or low. For the most part I was able to tell after a first date if there was any sort of connection.

That leads to an even greater question: Why am I still single? Simply put, the answer is that I’m not going to settle. If something feels wrong, I’m not going to ignore it like I’ve done for past relationships. I’m looking for an amazing connection with someone special. Not love at first sight–but at least some bubbly excitement from the beginning and through the first conversation. I had one like that recently that I’m curious about exploring. We’ll see what happens.

So that’s my story about Match. Maybe I’ll reactivate my account someday; who knows? For now I’m grateful for the experience, extremely grateful for the new friends I’ve gained, and relieved to take a break from all this.

17 thoughts on “18 First Dates”

  1. Very, very interesting. Thanks for sharing. You’ve given me some ideas on improving my profiles. I think I’d rather get an “I’m not interested” e-mail, versus being ignored. If I have to send it, I simply say, “Thanks for the interest, but good luck fining another match on the site.” But I can also take a hint if I ask questions for the first two e-mails, and all I get are short answers back.

    Has Biddy ever met a dog? I have the one dog afraid of cats. It’s pretty hilarious. She’ll hide behind my legs and bark at it, and later just make sure she’s on the opposite side of the room until she warms up to it. She would actually play with the rabbit I had though. Weird.

    • Yeah, I didn’t realize how hard it was to see the hyperlinks! Sorry!

      See, at the beginning of my time on Match, if someone winked at me and I wasn’t interested, I would click the button that says, “I’m not interested” and Match would send them a little message. But then I learned that some women don’t like that–they’d rather just not hear back (and I’m the same way). So I stopped doing that.

      Ooo, Biddy doesn’t like barking dogs. Too scary for him. He’s a big boy, but even smaller dogs are stronger and faster than him. I don’t want them to eat Biddy.

  2. Being hesitant that she has a dog (in the list at the top) seems incongruous with the comment that you shouldn’t let “future logistical concerns” impeed you from the first meetings. This leads me to the bigger question: Why do you have such expectations for this person??? I understand that you have learned from previous relationships, and I understand that you don’t want to settle. But dude, people are flawed. My best friends are very flawed. Superman is a lonely character because he isn’t flawed, and thus no one can relate. If I was with someone who was flawless, or exactly what I wanted (see The Survey), I suspect that I’d constantly feel inferior, and be trying to impress them rather than being myself. The relationship would be unbalanced, and I think I’d be miserable.

    Could you be Lois Lane?

    PS. 7 second dates is a relative number, even when you put it up against 3 months. How many first dates did you have? How many women did you communicate with? Shoot for a percentage. Help me to judge you better.

    • A fair point about the dog. Although it’s incongruous, it’s true–if I see on a woman’s profile that she has a dog, I feel a little twinge of hesitation. But it’s definitely not a disqualifying factor. I definitely don’t consider having a dog to be a flaw in any way.

      The title of the post is 18 first dates–that’s the number of first dates I went on. I probably exchanged e-mails with about twice that many (at least one e-mail). Match only keeps track of a month’s worth of data, but extrapolating that data for winks indicates that I’ve been winked at about 100 times, and I’ve winked (either winked or winked back) about 30 times.

  3. 36% chance of written communication after she winks;
    50% chance of first date after written communication;
    38% chance of second date after first date;

    OR 7% chance of second date for anyone who winked at you.

    As a numbers person (and one who forgets what the title of a post is as reading the post), I feel better.

    • Thanks for the percentages, Red. Those seem like awfully low percentages, a bit depressing considering it’s Jamey we’re talking about. I would have guessed his numbers were going to be higher.

      • Actually, having known a few other men on match and other sites (I contend that women’s percentages may indeed be higher), I think those percentages are pretty high. While Jamey was on match, I was present while at least 2 other men asked Jamey for advice or wondered what they were doing wrong because they weren’t even getting winks.

        • T, Winks are based on the profile and picture. So, those other guys don’t present themselves in the way that Jamey does. Either 1) they don’t actually have appealing goods to offer, or 2) they don’t present themselves well. Or Both.

  4. WOW! Thank you for writing about your experience on Match. This is something a lot of people don’t bother to think about when going on these sites, the amount of cost and time involved in putting yourself out there. If anything its a lot more pressure on men than it is the women and I think its something for people to take a step back and look at.

    You’ve offered up some interesting points and I especially like your part about, “She said, “Why does Biddy have to meet my dog?”” WHAT A REVELATION! I was very guilty of this when I was single and looking thinking immediately with long term goals in mind. Quite possibly it could have driven some of the guys away. (Which in the long run worked out for me! 🙂 ) I think those who do want something meaningful, think this way and there is nothing wrong with it but for immediate purposes of just feeling out the situation, it might be intimidating to their date. I’m so glad you pointed that out on here.

    It’s interesting what you’ve learned in this experience and I think you’re illustrating the things most people can’t put their fingers on when it comes to dating in general and website dating.

    Who knows, maybe during the break from Match you will find what you’re looking for? 🙂

    • Thanks Georgia! I’m glad you enjoyed the entry. And you’re right–if you’re looking for a meaningful relationship, there’s nothing wrong with thinking about important questions (especially about cats). I think it’s a combination of living in the moment and acknowledging long-term dealbreakers.

  5. 18 first dates – good god you MUST be exhausted! In about the last two months I’ve had 4 first dates, 2 second, 1 third. I’m just starting to get the energy to go at it again.


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