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I remember praying, legitimately, when I was 16 that I would not have to marry one of my guy friends. So they thought, “Hey, let’s see if we can’t help each other overcome these issues with a grand dating experiment.” The rules of engagement (pun intended): they had to see each other for the 40 days, go on 3 dates a week, see a couples counselor, and go on one weekend trip. We can have an unexpected conversation, see you do something cool/brave/impressive, discover a different side of your personality and–BAM–we see you in an entirely new light. Men, I would argue, have much more inflexible folders.
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It all comes down to how your friend feels about it. Remember, it’s a tricky situation and if you don’t do your homework, you could lose your best friend. If it’s been a few years and your bestie has definitely moved on, give it a go. You were a good friend and kept your feelings to yourself for long enough.
Pay close attention to when it is and isn’t okay to date her ex.
It was while planning this vacation that it hit me: The two longest relationships of my life have both been with men who I was never officially dating.
Boyfriends and girlfriends have come and gone, but my friends with benefits have stood the test of time. That’s longer than I predict my first marriage will last.
In response to the fact many of my friends are moving overseas right now, six weeks ago I decided on a social self-experiment: Can I use Tinder to make friends? "By the end of day one, I had matched with 30 people and initiated conversations with about 15.