There's a reason why you're reading this article. Everyone knows dating a friend's ex is taboo; it's an unspoken rule of society. Every so often, however, you find yourself in bad circumstances. Do you take the plunge or forever or wonder if you lost your perfect match?
Because situations vary, no golden guidelines apply in every case. How, then, do you approach the elephant in the room? Before you bite the bullet, ask yourself the following questions to decipher whether it's okay or totally off-limits. At the end of the day, listen to your gut instincts to know if it's safe to proceed.
1. How many years have you invested in the friendship?
Obviously, you will feel more comfortable talking to a friend you've had for years. If you're acquaintances who can go weeks or months without speaking, you really don't owe them more than a heads up. Closer bonds are worth more than a spring fling, so take it all in stride. Would you care if all ties were severed? Will you lose other friends in the process? Romantic involvement with an ex will cause irreparable damage, so prepare yourself for the worst.
2. Was the ex dropping hints?
If the now ex-beau was sending you cues during the relationship, like being overly attentive or outright confessing their secret feelings, you know they are interested. However, if they couldn't respect your friend enough to break up before flirting, why do you think they desire exclusivity? Chances are this person is not very good with monogamy and will treat you the same way. Soon, you'll be the one complaining about a friend who disregarded your feelings and dated your ex.
3. What kind of relationship is your friend in now?
If the friend has moved past the ex in question, it may not be as much of an issue as you assume it will be. Best case scenario, they progressed to a long-term entanglement or marriage. Declare your intentions and ask if you can make the process easier. Unless your friend unearths some deep-rooted regret, you're safe to proceed. It's also important to discover if they left unfinished business, or you might open Pandora's box. Make sure both parties exhausted all possibilities and are not open to reconciliation. If the ex is your friend's "one that got away," leave it alone.
4. Did you provide advice to either side?
Were you the sounding board when they were together? This can work against you, because your friend can perceive former helpfulness as a hidden agenda. You lent an ear, but you also learned everything you could about the other person. You know what works and what doesn't. Even if you never planned for the current situation, your friend will forever doubt your previous intentions.
5. How serious were they?
A month stint will prove less of a conflict than a three-year love fest. Anything under 6 months is up for debate, but deeper feelings may still be at play in casual relationships - especially when it involved intimacy. If your friend seems hesitant, tread with caution. You won't want to date anyone they keep in touch with and regularly hang out with, because it will cause awkwardness in your social circle. Always avoid dating the ex of a divorced friend. Unless you earn a rare blessing on both sides, your friend's ex is a forbidden fruit you should never taste. That experience can get uncomfortable very quickly.
Dating a friend's ex should be evaluated on a case-by-case basis. While it can develop into a quality connection, it often results in losing a friend for a relationship that doesn't last. Maybe you possess an unshakable bond, and nothing will tear you apart. Most friendships, however, will not be able to withstand this kind of stressor. If you honestly consider their ex an unbelievable opportunity, express this clearly. Have an adult conversation and don't get defensive. It's natural for them to feel apprehensive and exploited. In the end, you must only ask yourself one question: Is this friendship worth losing