Being Aggressive About Meeting without Scaring Her Away

Published on July 23, 2012

If you’ve read my dating guide, you know I’m for meeting quickly when using online dating. However, there are times where the approach of trying to meet quickly may not go over well with who you are communicating with. Here’s one example from a reader:

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. I know she’s busy in the real world, working and studying in the evenings, but 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 her off by doing it too soon, before I’ve established trust.

In this case, my reader was a veteran of online dating but questioned the idea of jumping to a first date because of her hesitation about online dating and the fact that she had yet to make it to a first date.

Being Aggressive with Meeting

This issue shows that there are rarely “right” answers with online dating. Moving rapidly to meet might work great with some people, but in this case moving rapidly might ruin the chances of meeting. Because of this, I want to talk about a few approaches to this situation.

My Personal Approach
After I had been dating online for some time, I really didn’t have the patience for women who were both dating online but at the same time not really dating online. I know there are women who feel the same way: those who grow tired of communicating with men who would email them again and again and again but never ask them out.

Because I was dating in such a way that gave me opportunities to meet a lot of women, I would generally ask a woman out, at the most, three times and after that I’d move on. I’d try to build some trust between the two of us and would space out my attempts at asking her out. However, if she was still giving me the run-around by the third time I asked, I would generally start communicating with someone new.

I feel this worked well for me and honestly I can’t ever remember having a woman from this type of situation contact me and say: Why’d you stop emailing me?! If she were really interested, my “disappearing” would have bothered her and yet it never did. So perhaps these women weren’t interested and my moving on just saved us both a hassle. However, I also think this is a sign that some people are online but they don’t really intend to meet anyone. I honestly feel that some people are sad to be single but feel relief when they see a dating opportunity pass them by. It might be fear or a busy schedule or whatever, but there are some people who like communicating online but just aren’t ready for more than that. That’s fine, I just don’t want to spend all my time chasing someone like that.

Situations that Deserve More Patience
So the above was my preferred approach. However, if you feel there is a strong connection that’s worth being patient for, I’d recommend concentrating on moving the conversation to the phone or Skype if you already haven’t. This seems like a nice “step” for someone who is nervous about dating online: it can show that you’re real and perhaps remove some of their hesitation.

That being said, I wouldn’t spend too much time chatting on the phone or you could end up in the same situation just with a different way of communicating! I’d suggest attempting to schedule a date after two or three “substantial” conversations (let’s call substantial 30+ minutes each).

Once you have the phone/Skype out of the way, I would recommend trying to get her to meet in the easiest and safest way you can think of. For example, you could recommend:

• Meeting for a quick coffee somewhere very public. Limit the time you’d be together to 30 minutes or even 15 if it comes down to it.
• Suggest meeting up at a local park for a walk and you’ll both bring one of your single friends as well.
• Make the meeting seem less direct by making it a by-product of something else you’re doing. For example, you could send an email like:
  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 before I have to catch my flight (or whatever it is you’re doing) but I wanted to have a chance to meet.
• You could even suggest to having her friends meet you first…although I think that’s a bit much.

Honestly, as I write this list of ways to convince someone to meet, I’m reminded why I gave up on trying to convince women to meet at a certain point. It all sounds like a big pain to me now. However, if you’re feeling a really strong connection, hopefully trying to work around her fears could encourage her to meet.

If she’s not willing to talk on the phone or every idea you come up with to make her feel more comfortable isn’t good enough, it’s time to move on. Either she’s not really interested in you or she’s not really interested in meeting anyone.

One Final Warning About Fighting for the First Date
My experience was that the harder I had to work to get a woman to meet, the more likely I was to be stood up on our first date (or in some cases having her cancel at the last minute). I remember one woman in particular where I worked hard to get her to meet me…and I probably even broke my only-ask-three-times rule with her. She finally agreed to meet me but then stood me up. I think I had talked her into meeting when she really wasn’t comfortable with it yet and she basically chickened out at the last moment.

So, keep in mind the fact that being stood up does happen. When you’re planning that date, make it something that will make your life easier if it does happen. It’s a lot easier to be stood up at a park than it is at a restaurant where your waitress and you both know you’ve been stood up but neither of you want to say anything!

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