Online Dating Blog

I’m a big fan of getting to the first date quickly in online dating. I wrote about this in detail in my article on planning the first date. I didn’t realize this when I started my website, but it turns out that lots of people giving online dating advice hold this opinion too.

Personally, I had success with this approach. But one reader contacted me with some doubts:

Online Dating and Giving Yourself More Opportunities

The way this reader ends his email sums up my frustration and why I abandoned waiting weeks to ask a woman out: it wasted so much time.

In answering, let me start with this: I think each person needs to take the approach they are comfortable with. If you have patience and feel that you have a lot of success talking to one person for weeks at a time, I’m not going to say you can’t find a great person. As this reader points out, in my online dating guide, I talk about how I think one thing where some dating advice goes wrong is suggesting that there’s only “one” right way to do things. I don’t agree with that.

Here are my thoughts generally on asking a woman out:

1. I generally asked a woman out around the third email. In some cases, such as with the woman who is now my wife, I even asked the woman out in the very first email I sent. Remember: dating online isn’t about staying online. You do actually have to meet at some point so I avoided unnecessary delay.
2. One exception: I’d wait longer if she said she was new to online dating or if she seemed nervous. I was also in my twenties and perhaps if I were in my sixties with lots of people who were openly uncomfortable with online dating, I’d probably slow things down. Things do change from opportunity to opportunity.

The reason I asked women out earlier is that I found that I was spending a LOT of time talking back and forth for weeks or even months and then when we met in person there would be little or no chemistry. This meant that I ended up spending a lot of time talking to a woman online or on the phone not knowing if we were a match, where spending just five minutes together in person made it clear we weren’t going to work.

So for me, it’s about spending time on the right woman. If women say that it’s creepy to ask her out in the first few emails, I’d ask: what are you asking them to do? Because I rarely started with dinner and a movie or anything that required a big commitment. Instead I would recommend coffee and I’d let the woman know I only had 30 minutes to meet (even if I had longer). This way, there was less pressure because it wasn’t a full date, such as dinner and a movie or whatever. She’d be safe, she knew I didn’t have all night, and lots of women said yes.

The Risk of Scaring a Woman Away

There is an argument that if you ask a woman out too quickly, that you may have cost yourself an opportunity. I think that you cost yourself a lot more opportunities by not asking women out quickly. If you spend weeks on a woman and then when you meet it goes nowhere, that means for all those weeks you could have been pursuing many other opportunities…but you weren’t.

So, sure, it’s valid to suggest that you’re taking a risk asking her out early. But I think the risk is greater if you don’t. That’s my take on it. For those of you who feel you can only have success with weeks/months of communication first, I’d say keep doing that. But if you can get to a point where you can get to the date sooner, I think you’ll improve your odds on meeting the right man/woman.