The pros and cons of dating an ex

Find out when it's good to go back, and when it's best to say goodbye

There are two types of break-ups: the ones that stick and the ones that slide. Find out when having an ex around is a good thing, and when it’s time to cut each other loose.

Situation #1: The wedding date
Every single woman of a certain age needs a go-to wedding date and an ex is often the best choice. You can flirt without feeling obligated or hook up without feeling like you’ve added another notch to the bedpost. You’ll have a slow dance partner and someone to hold your shoes at the end of the night. But don’t get caught up in the romance and make a mistake. Erin, happily single in Halifax, took her long term ex to a wedding three months after they had mutually decided they didn’t want to get married. “We got back together for one more month before we realized, this time under not-so-friendly circumstances, that we weren’t right for each other,” she says. “I lost a friend, and it could have been avoided.”

Situation #2: The work party
Sometimes work functions feel like a loved-up Noah’s ark, with happy couples parading around in twos. If your colleagues are mostly married, it can be soothing to have a familiar face by your side. This is for friendly exes only – the office Christmas party is not the place to create public tension. Keep it informal and introduce him by name, not by relationship label, “This is Joe, Joe meet Jane,” and let people assume what they want.

Situation #3: The random hook up
Running into an ex when you look your best is like finding the perfect pair of jeans: elusive and extremely satisfying. Sometimes, it can fire up sparks you thought were long gone. “I hadn’t seen [my ex] in two years and all of a sudden there he was at a friend’s engagement party, alone. As soon as we saw each other, I knew we were both interested,” says Kyle from Toronto, who is recently married. “We flirted like crazy and ended up leaving together. It was a great night, and we didn’t see each other again, which suited us both fine. It was the perfect way to put the case closed sign on our relationship.”

Situation #4: The lingerer
Sometimes it’s easier to go back than move forward for a reason. If you still have feelings for an ex that show no signs of dissipating, it’s better to confess than to wonder what if. It’s difficult to make yourself vulnerable to rejection, but you’ll thank yourself when there’s one less thing to worry about. “I kept comparing guys to my ex from a few years back without really realizing it,” says Melissa. “While I was out West visiting my sister, I phoned him, we went out for coffee and ended up falling in love all over again. I moved to Vancouver and now we’re engaged and buying our first house.” If you get the happy ending you hoped for, reconnecting with an ex can be more than you ever imagined.