Online Dating Blog

Sometimes I reference my experience in my other posts and while I discuss my dating history in my guide, I wanted to have an article I could make references to that anyone could see. I’m not going to go into extreme detail but this should give a nice overview of my online dating experience for those interested.

The Failure Phase

I started dating online in June many years ago. I had actually thought about signing up for an online dating service for months (maybe even a years if I’m honest) but couldn’t bring myself to do it. As I mention in my guide, I believe it took my loneliness to outweigh my pride before I started taking online dating seriously. The first time I signed up for a dating service was impulsive: I found a woman who seemed interesting and who seemed very accessible based on her profile and who also lived in my home town. So even when I finally did give online dating a chance, it wasn’t so much about planning as it was about making a decision on the spot.

My first dating profile photo…not particularly good

I was a little too satisfied with myself though and I had no idea how to move forward with the online dating process. Looking back, I can see that she was dropping hints that she wanted to meet but I was just too blind to how the process should have gone. At the time, I thought “Online dating is risky so most women will probably want to talk a month before we meet. If I ask her out too soon, she’ll never talk to me again.” If you have read my online dating advice, you know that I now believe this is an incorrect way of looking at online dating and I encourage my readers to meet other singles sooner rather than later. At any rate, I suspect she eventually became bored of waiting on me as she “disappeared” (that is, stopped responding to my emails). At the time I was very confused as to what went wrong.

For the next few months I basically had no success at all. I believe this failure was due to three issues with my approach:

1. First, my initial success contacting the first girl had me convinced things were going to be easy
2. Second, I was convinced that the most appropriate way to approach communicating with women was one woman at a time. I would email a woman, wait a few days and then if I didn’t get a response, contact another woman. This approach caused me to have very limited online dating opportunities.
3. Third, I still believed that women would want to talk for weeks or months before meeting.

If you look at the second and third bullet, these two approaches together create a very difficult dating environment to have success.

A First Date
Time passed and I found myself a few months into online dating with zero first dates and I felt horrible. However, in August of that year, I started to communicate with a girl who had a similar philosophy as me: talk to one person for a long time before meeting. With her, my approach actually worked, although it took over a month to meet. When we did go out, which you can read about here, it ended very poorly from my point of view. I found this depressing because I at that point I was approaching 4 months of dating online and only had one bad date to show for it.

After that point I went a few more months with basically no success. I was still going with the one-conversation-at-a-time approach so my opportunities were limited.

The False Success Phase

In the fall of that year, I had my first good date which ended up with us dating for several months. However, I was just making a new mistake in this case. We didn’t get along at all! We had totally different outlooks, we disagreed on some pretty core areas of our life and (for reasons still unclear to me) she went out of her way to keep our relationship a secret from her family. There were very few merits to the relationship and it was a horrible choice to continue dating her once I realized this.

However, at this point in my dating life I was more concerned with having success (however small) than I was with having a good relationship. I wanted to be able to say I was dating someone more than I wanted to have a good relationship. Over five months of failing with online dating had caused me to reach a point where I would accept any relationship, no matter how bad.

Fortunately, she broke up with me after a few months as she was moving away for a job. I was hurt by it at the time but looking back it was the best thing that could have happened (for both of us). Partly because it wasn’t a healthy relationship but also because it caused me to question my entire approach. I knew I was in a bad relationship even while it was going on but I fought to keep it going.

In some ways, this was same problem I was having with online dating in the first place: I was trying to make something work, no matter how many facts were presented to me that something needed to change.

I decided to reevaluate my entire approach to online dating and why I was dating in the first place. I committed to reading more dating advice both online and offline. Some of this advice was helpful but I found a large amount of the advice (especially much of what I found online) to be lacking. This experience with dating advice is what eventually led to the creation of this site, but that’s a story for another day.

The Success Phase

By January, I wanted to change how I was dating: I finally realized my failed approach was only going to continue to fail. I decided to approach my online dating life systematically and not just stick with what I thought was the best way to date online. I was going to be intentional about having success with online dating by trying the advice of others and also by simply experimented with how I was approaching writing emails or creating my profile or when having a first date. I didn’t have any “success” in January but I do consider this time period to be the turning point for my online dating life, from bad to good.

I started asking girls out more often and much more quickly. In the beginning (early in February) I wasn’t having much more success but I kept at it. I started trying to date just about anyone, if only to get more experience figuring out what worked and gaining comfort with all the first dates I knew I would be having.

It took a time but eventually I found myself with a date every other week, then I improved to one first date a week and at the end I found myself going on multiple first dates every week. The great thing at this point was I felt so great about all the dates I had planned I started asking women out in the “real” world. This is something I had never done before and I was even having some success there (lots of failures too though!) I had lost my fear with meeting women or first dates because I had so many opportunities a single failure meant nothing. Compare that to when I was attempting to talk to a single woman at a time where a failure meant everything. A single failure when talking to a single person meant starting from scratch. A single failure when talking to 5 women meant little more than that my schedule on Tuesday had just cleared up.

I met the woman who would become my wife in June, one day short of a full year of online dating. I knew right-away that we had something special and that night I contacted the other women I had scheduled dates with and canceled. I ended up calling 5 or 6 women, which was just another reminder of the turn-around in the success I was having. By the end, I had just as many first dates scheduled for the next two weeks as I had had in the first 9 months of dating online.

Looking Back

So what’s all this mean? Basically, it comes down to the fact that I dated online very actively for a full year and for 8 or 9 months of that time, it was a miserable process. The last 4 months were the exact opposite: interesting and exciting. I was really having fun. Even though I was thrilled to meet my wife and even though I immediately knew we were going to have something special, there was a part of me that was sad to see online dating go because I was finally doing it in a way that made the process of dating very enjoyable.

I wrote my guide with the hope that it would help others get to the “fun” part faster. That said, it is work. Even though I feel very comfortable with dating online now, I’m not going to kid myself and suggest that if I started dating online again tomorrow that I would immediately have tons of first dates right off the bat. It takes real work even when you know what you’re doing.

The biggest turning point was when I decided I would date women even though I strongly believed it wouldn’t lead anywhere. If you can change your goal from “I’m going to find and then date the perfect person” to “I’m going to date and then find the perfect person” you are going to have more success, in my opinion. I never plan on being single again but if I were I know I would follow this rule because it worked so well for me before. It didn’t just improve my online dating life, it improved my dating life. I found myself talking to women in the real world, asking them out even knowing it would likely go nowhere.

One other note: Kate, my wife, didn’t have a photo in her profile. My “old” approach of finding the perfect person and then dating her would have never allowed me to contact someone without a photo but my new approach did and it made all the difference.

Online dating is frequently frustrating and often can create a sense of hopelessness but I honestly had fun dating online the last 4 months. I stopped looking at women as a solution to my problem and started seeing them as people I could meet and have fun with. I stopped taking things so seriously and started giving everyone a chance (well…everyone within reason!)