Asking Out Online Daters Who are Nervous with Online Dating

Published on August 1, 2011

A reader wrote in that he was talking with a woman on an online dating service but she was very nervous about actually meeting someone using the service. Here’s his question:

I’ve been emailing a girl on Match.com for a couple of weeks now, and I’m struggling to work out where I stand, and how best to develop the email conversation into a real date. The girl has a really nice profile but took a few days to respond to my first email, and doesn’t seem to be online that frequently.

…she also says that she’s wary about online dating and hasn’t actually had a real date through the site yet. I want to ask her out, but I don’t want to ‘scare the horses’ by doing it too soon, before I’ve established some kind of email rapport or won a degree of her trust.

I remember feeling this way talking to a few women…one in particular gave me a very difficult time about meeting. Eventually, after I had been dating online for a while I really didn’t have the patience for women who were both dating online but at the same time not really dating online. I was pretty quick to ask women out on a date and if they didn’t respond I was quick to move on. If they did respond but wanted to wait, I was fine with that but generally I would continue to ask once a week and after the third time they said they needed more time I stopped asking.

However, if you do feel there could be a strong connection that’s worth being patient for I’d recommend you instead move the conversation to the phone. This seems like a nice “step” for a woman who is nervous about dating online. That being said, I wouldn’t spend too much time chatting on the phone. Maybe 2 or 3 substantial conversations (30+ minutes each) and then try to move it forward to a first date again.

At that point it might be something as simple as getting her to meet you for 30 minutes for coffee. You want to keep the first meeting short so that it doesn’t feel too much like a date (or in her mind, a “big” step). If you know the general area where she works or lives, you even try an email like this:

Hey I’m going to be in your area this Tuesday and was wondering if you wanted to grab a coffee. I’ll only have about 30 minutes but I thought it would be great to talk in person for a change.

If she’s willing to do that, moving to a real date will be easier.

If you find yourself in the same situation as my reader and they are not willing to talk on the phone or meet for coffee then you’re going to have to decide if it is going to be worth the patience and effort (I generally decided no, it wouldn’t be).

Like I said, I eventually got to the point where if they weren’t interested in meeting me, then I wasn’t interested in meeting them. I wasn’t looking for a pen pal or a new friend on Facebook; I was looking to date. So if you’re in this situation I’m all for giving them many chances to come around to the idea that meeting someone from the internet is okay but you definitely have to draw the line at some point.

The eharmony Difference? Deep compatibility! Try it Today!

Posted in: