After nearly five years together, I recently split up with my fiancee. We remain friends. Her best friend has also recently become single, and we have been hanging out a lot lately, in groups. I always had an eye for her but passed it off as the allure of forbidden fruit. Is my attraction to her a reminder of days gone by? Is it just that she is familiar and convenient, or are my feelings genuine? And how do I broach such an awkward subject with someone who has been my friend for so long?
Convenience does have its exciting side. But make no mistake, opportunity can certainly give rise to real feelings. The issue, however, isn't just whether your feelings are genuine but whether they are reciprocated. Otherwise, there's no possibility of a relationship. To find out whether your attraction is durable, spend time with your friend in a variety of situations, both in groups and alone, and also spend time outside the group, with others. The big challenge is to organically engineer some time alone together to communicate your interest reasonably clearly and to see whether it is welcome. The ideal is a small step forward that requires some response on her part but not so big a move that, if it failed, you would feel awkward staying in the group. You've lost a fiancee; you don't need to lose your whole social world. Use your knowledge of the way things usually flow in your group to plan the right time to approach your friend about splitting off from the others—maybe for dinner together or some activity that evolves out of what you have been doing all along.
