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Is There A Line That Shouldn’t Be Crossed While Dating Multiple People? I think that if you’re dating more than one person you shouldn’t be having sex with any of them. I know some people who feel that this is totally fine, that’s just not my opinion.

If you live in fear and insecurity, you are going to meet someone exactly like you.

The rule of thumb I’ve started to use is that if I like them a decent amount, and I feel like things are going well with them I will mention that I’m seeing more than one person by the third date.

I tend to feel guilty dating more than one person if I sort of care about one of them, so if I feel guilty I’ll speak up and just keep everything out in the open.

While this may be true of some women who are dating multiple people, I actually believe that there are many good (and, in fact, great) reasons to date several different people when you're single.

I even think that dating many people might be one of the best ways to find the one person you are really looking to find.

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You’ll start to hope it’s a certain person when your phone rings, you’ll be more excited about plans with that person.

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