Dating in 2007: A Male’s Perspective (Part 1)

waiting for a date to arrive

Where is our generation’s equivalent of Cather in the Rye? I feel there is not yet a book that has come to define our new era of social media and living lives increasingly online. Dave Eggers is probably our greatest hope to write such a work. In the interim, I thought I’d share some thoughts on a topic relevant to many readers here: the state of dating in 2007.

I’m 27 and single. I would love to be in a fulfilling relationship with a great woman who I might one day marry. I know most of my friends both male and female) feel the same.

Many of my single friends should be very eligible candidates: exciting jobs,  well educated and above average looks. However, I get the sense many of us have become jaded by the current culture of dating.

Exposure and Choice

There is a tremendous book I read recently called the Paradox of Choice. Many of the book’s central tenants resonated with my own experience dating. The key argument is that despite the increase in choice we currently have as consumers (from salad dressing to blue jean brands) our overall levels of satisfaction have actually decreased. Takeaway: more choice does not always lead to more satisfaction.

I see an analogy with dating. One of the most successful relationships I can think of is that of my grandparents; happily married for over 60 years. My grandparents are likely not too dissimilar from many other couples from the World War II generation. They lived in small neighboring towns in New Hampshire. They had a limited dating pool (constraints).

In my lifetime, by age 27 I have likely been exposed to far more potential mates than grandfather had been. I have been fortunate to have lived in some of the greatest cities. I go out a lot but also have access networking events, dating website, cell phones, IM, etc, — a level of connectivity and discoverability that did not exist in the 1940’s.

To state the obvious, my total exposure to potential dating partners is an order of magnitude greater than was possible just a generation ago. And yet, I remain single.

My contention is that while I believe online dating will become the norm — the byproduct of massively increased exposure and choice  is not necessarily better. My grandparents restraints (geography and communications) produced one of greatest relationships I know.

According to the Paradox Of Choice:

1) It’s difficult to enjoy something when you know there are so many other alternatives (the grass is always greener)

2) With more choice and more sophisticated media, expectations increase dramatically

3) Trends of modern society are devaluing offline relationships


With so much access to such large numbers and varieties of people, it’s difficult to avoid a mindset of sampling. For example, if I go out with someone and don’t immediately hit it off, there is likely not going to be a next time. The danger of this is that relationships and people often need time to develop and bloom.

With greater choice and exposure we expect that we can always find better: a grass is always greener perspective. Growing up I was told never to settle: this is a great mentality for business — but not necessarily for people. What is good enough? Also over optimizing for specific compatibility or character traits is exhausting. We have been trained for a new type of consumerism: researching, critiquing, waffling with purchases and that behavior threatens to carry over in evaluating people.

Another important point is that media skews our expectations: many of us have unrealistic expectations. We live in a culture of media that values the most beautiful people. I recently heard a lecture on how watching pornography can destroy a male’s ability to ever enjoy sex, as their expectations of how a woman should look or act become twisted.

Finally, the trends of modern society are moving us away from the practice of developing deeper relationships. Why talk on the phone, when you can text message? Work is now 24/7 and consumes so much of our time and identity that we prioritize work over relationships.

Overall, dating and the movement toward online dating is a positive one. However, the key is how to leverage our increased exposure for the better without being consumed by the paradox of choice. How can we use technology and the Internet as a force for good in building deeper, meaningful relationships?

Read Part II

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