Everyone Is Doing It This is less of a rule and more of a fact to keep in mind: Yes, that may be an awkward conversation. Just talk about it and you won't have to think because you will know. As you're parting, look about yourself a little bashfully and ask something suitably rom-com, like "Would it be crazy if I really wanted to kiss you? There is no guarantee that the other people involved feel the same way, or conduct themselves along similar lines. So do it!
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Dating more than one person at a time
I highly recommend communicating more than less. There are benefits to dating more than one person at a time. Is it cool to date more than one person at a time? And that went for dating as well. I've never been on a date via online dating website, but I'm not sure why it matters in the context of this question that you met these women online. That way they can make informed decisions about their sexual and emotional health. You want to at least meet him and see how the two of you hit it off.