Taking a trip with a male friend? (wife, women, family)
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No problem.... Separate rooms to assure a good night's sleep.
Seriously... It really depends on the relationship and the boundaries the friends have established. Intimate friends it wouldnt be a problem because the awkwardness has been worked out. Platonic friends would be awkward.... Unless there was a bunch of us and we just needed a place to crash on a budget.
I have a female friend I have known for almost 30 years, there was an initial attraction, but due to the fact one of us was always in a relationship we never hooked up as a couple although we became best friends.
I lost touch with her for a while after my crazy ex wife was jealous and it got awkward to see her, but we reconnected a few years back and the friendship went right back to where it was.
I wouldn't think twice about going anywhere with her, and I would no more try to bone her than any of my male friends
Guys would you take a trip with a long time female friend?
Would it be weird? What if in the past you were intimate?
It brings up the old conundrum of can guys be friends with women?
I did this last month. I took my dear friend - and former FWB of 5 years - to where I'll be relocating soon, for 5 nights. We shared a bed, but not sex (she recently became exclusive with another good friend of ours we introduced her to, and no one wants to mess that up). My wife and I want to persuade her to relocate there as well, as there are good opportunities and she has no other people where we currently live who are like family (hers is half a world away). The friend to whom we introduced her also knows about the trip, and he is considering relocating as well.
To me, there is no conundrum: men and women can be friends, and not cross boundaries even when there is every opportunity to do so. It does require integrity to choose to do the right thing, and a little self control.
Location: Huntersville/Charlotte, NC and Washington, DC
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Trip with a female friend, no biggie.
A trip with some friend I’ve slept with, hell no. I’m very adverse to awkward situations.
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Friends are friends. Who cares if they are male or female? 
