The “friendship with benefits” is one of man’s most logical creations. Consider the symmetry that results when a consenting male adult who wants no strings attached sex, combines forces with a consenting female who wants sex under similar circumstances. Still, there will come a time when these goals no longer align, or for some reason or other you need to end the arrangement. How you should do so will depend on the reason.
You Both Want Out
This is the ideal reason. Perhaps you’ve both outgrown the arrangement, or are entering into committed relationships. We suggest having the same direct discussion that led to the arrangement in the first place. By this point you should have a good idea whether you will remain friends with this girl or not. One topic you should get her to agree on now, if you haven’t already, is whether you will be keeping this from your future girlfriends or boyfriends. In olden days, a well-bred man would give some token of appreciation to a parting mistress for all the fun fornication. You needn’t do anything as formal as dinner but we don’t see any harm in having one last good time together.
She’s Become Attached
Even if you both had the best of intentions, it’s not surprising if she or you (probably her) has developed romantic feelings that were not in the original plan. If you realize or suspect that she’s developing the kinds of attachments that you wanted to avoid, it puts you in a dilemma. Presumably you like the girl, but the reason you wanted this arrangement in the first place was because a relationship was not something you were willing to deal with. At least, not with this girl, don’t succumb to the temptation to avoid the problem. That’s an easy out that’s not really an out. Attachment is just one of the risks of this kind of relationship. Under these circumstances, all you can do is end the situation quickly. You can try to be nice and explain your reasoning, but be aware that talking will not do much good. You can’t talk someone out of having romantic feelings. We don’t recommend continuing to sleep with this girl, even if she agrees to it.
If she’s reasonable she won’t treat like you a villain. Under these circumstances, a farewell gift or fuck isn’t appropriate. You can express your appreciation about her but be prepared for hurt feelings. Hopefully the friendship can continue, but as you always knew, there was never a guarantee.
You shouldn’t take ending a friendship with benefits lightly. We applaud your maturity in coming to this realization, and taking the time to evaluate your approach. Hopefully you’re left in a position better than the one in which you started, with your friendship intact, and lots of good sex to show for it.