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Where do you draw the line between being flirty and flirting?

I'm not sure how to phrase it. I want to be more flirty with my friends. You know, like touchy, cuddling, and stuff, but not as a means to pursue them sexually or romantically. I can't think of a way to phrase this other than "being flirty" versus "flirting" (let me know if you have a better word). I just want to have that physical contact and flirtatious banter but not in a way that makes them feel as if I'm trying to get them to sleep with me or fall in love or something.

Background, I'm a happily married man in my early 30s. My wife and I are bisexual, I'm still mostly closeted and she's out. My wife and I have discussed boundaries and we both know what each other's limits are. We did this because some folks we are friends with had a horrible experience with trying to have an open relationship but one of them kept breaking the rules they set forth so at some point the conversation came to what our limits are. To be totally clear, we aren't pursuing an open relationship. The limits we have are basically touching other people (not genitals) and kissing (not on lips) is fine and don't start to hang out with people "romantically" (a sort of "know it when I see it" thing). The two of us have said how we want to be more physical with our friends and even flirty at times because we both like to express love like that but we were raised in the Bible Belt in Christian purity culture and have a hard time figuring out how to do this. For some people it just feels so natural.

Some examples of things I might want to do are

  • Hold hands or put my arm around them
  • Make flirty remarks about their outfits being attractive
  • Kiss ya homie good night (I say this as a joke mostly but haha jk, unless?)

An obvious answer may be "just ask your friends, you had the same conversation with your wife" but some missing context is that this conversation with her culminated with the boundaries discussion but has been happening slowly for a few years. We've tossed the idea of open relationships around and both decided against it because we don't believe either of us would be able to not get jealous. I'm very concerned that just asking something like this out of nowhere would seem creepy and off putting. On top of that we do have some friends who have seemed to express they wouldn't like this. Obviously I'm not going to do this to people who I believe wouldn't like it, but it concerns me that more people have this opinion than I think.

So, I guess the questions are,

  1. Have you tried to do this with friends? If so, how did it go?
  2. Where would you personally draw the line between "flirty" and "flirting"?
  3. Have you ever tried to ask platonic friends about this? How did it go?
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