Feeling blah about internet dating

I got this letter during the earthquake so I figured I should answer it quickly. Letters seem very urgent when the ground starts moving as you read them.

About 6 months ago, I broke up with my boyfriend of several years. It was clear we were on different paths and wanted different things in life so we decided to part ways. It was a very mature break-up, but was painful nonetheless. I've tried to stay positive about things and embrace my new found freedom.

Fast forward six months -- I've relocated to the Boston area and landed a great new job! Everything is going really well in my professional life. In my love life, errrrr, not so much.

Recently, I decided I was ready to start dating again, so I joined Match.com. Truth be told, I would prefer to date the natural way, but I've found that I'm not meeting new men in my day-to-day life, even being in a new area. I don't have many single girlfriends to go out on the town with. All of my friends are married or in serious relationships. Also, I work in a very small office, so there are really no prospects there (I met my last ex at work, but we worked for a very large company).

I've been out on dates with three guys since then. The first dates have all gone fine, but I find myself losing interest quickly after that. I don't feel any connection with these men. I feel like I'm wasting both my time and theirs by continuing to pursue it, so I usually drop it around date #3. I understand that I'm not going to have a deep connection with these men right off the bat, that something like that needs time to develop. But shouldn't I be feeling something at least?

– Dating, Mass.

The question here is, "Should I feel something within three dates?" And my answer is, "Not necessarily."

I know, I know. It's annoying to keep dating someone who might turn out to be blah. But in the real world, it can take weeks before it occurs to you that the cute guy at work has an incredible personality.

I'm not suggesting that you go out on nine dates with every dud. I'm suggesting that you vary your dates. If you like a guy enough to see him a third time (and that's significant, by the way), make that next date different from the others. If you've had two simple dinners, go bowling. See a ridiculous movie and watch how he responds to it. Maybe (if it's not weird) invite a friend on the date to see how he deals with other humans.

You might need to see these guys outside of a restaurant in order to really understand who they are. Make that third date count. Give it the right context. Make it feel like the real world.

Readers? She doesn't seem to dislike these guys. Is she giving them enough of a chance? Can you get to know someone by having dinner with them a few times in a row? Am I wrong about giving the date a different context? Discuss.

– Meredith