Love Letters: Caught In The Web

Online dating presents a lot of challenges. It’s an incredibly common way to meet people, everyone’s using it. But that doesn’t mean that we all know the best ways to use it. I thought the two questions below were really on point, so read up to learn about how to handle two classic online dating issues.


Q: I’ve been emailing with a guy on an online dating site for over a week, and I’m confused about the next step. Do I ask him out? Does he ask me out? This is weird.

A: Totally common problem, with a very simple solution. In general, it’s best to participate in no more than 2-3 emails before setting plans to meet in person (for coffee, a drink, something quick if you’re timid about the whole process). Any more emails than that, and you’re into a weird zone where you think you know the person, but really you don’t. Also, you have to ask yourself, why is this guy on a dating site? To meet people in real life, or to make pen pals? Many girls like to wait for the guy to make the move and set plans, but I think it’s okay for either party to suggest a meet up. If he (or she!) waivers after plans are suggested, it’s best to move on to someone else. You only want to be communicating with people who are using dating sites for the same reason as you–to date!

Q: I get instant messages from guys on OKCupid all the time. Should I be writing back to them? I sometimes feel like I’m getting attacked with all of these messages popping up, and I have no idea who these guys are. What is the etiquette here?

A: OMG disable the instant messaging function of ANY dating site you’re on. No good comes of it. Similar to the answer above, it leads to getting caught up in this weird zone where you’re IMing someone you think you know, but you’ve NEVER MET. Disable. Do it now.

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9 years ago

I’m dating a man nearly four months but we are not boyfriends, I know his family and I sleep once a week at his house … I spoke in dating and he said that this is not accustomed to relate to and asked me to be patient, what do I do??

9 years ago

sorry to intrude but it sounds like you are already “dating”just without the commitment.

9 years ago

Shani, I SO agree with you on both of these things!!!!! I was once in contact with a guy for probably a month before ever meeting him, and when we finally met, it was really hard for me to realize that this idea of a person I had created in my mind did not actually exist. So weird.

9 years ago


PS. It’s only been two weeks without them, but it’s been a hard two weeks.

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