Swimming with Sharks: Dating in Your Ex’s Pool

Published on Author GG RayLeave a comment


For many, it is difficult to get back into the dating game after they have gone through a break up. Once you have spent some time of relative calm in a relationship, it is intimidating and often frustrating to have to get out there again and try to impress someone enough that they want to see you again, but not so much that they have left six messages on your machine by the time you get home from the date.

One problem that you will encounter, no matter how large a city you live in, is that once you get back into the dating world, the chances are unnervingly high that you are going to end up meeting someone who somehow knows your ex. It’s inevitable. It’s the cruel twist to the often delightfully small world we live in.

How you react to the revelation that the person you are dating, or want to date, knows your ex will depend on several things. First and foremost, it will depend on how long it has been since the breakup. If it is quite soon after, you will need to watch for a few possible reactions. No matter how much of a monster your ex was, resist the urge to bad-mouth her. Not only will you come off as bitter and clearly not ready to date other people, that information (whatever you have to say about your ex as well as how clearly upset you still are about the breakup—and whether you are upset or not, that’s how that kind of behaviour reads) is going to make it back to your ex.

As soon as you seem a little cracked when your ex comes up in conversation (whether your date knows them or not), it is a clear warning sign (for healthy people anyway) that you are not someone they will want to get emotionally invested in. And as soon as they have decided that, what do they have to lose dishing a little dirt about you back to your ex?

Another thing that any future with this new love interest might depend on is how close they are to your ex. If they are simply acquaintances or friends of friends, the most that will happen is that they might fish around for some information regarding your past relationship through mutual pipelines. If you tell her why you broke up, and again, best not to dwell on this topic for too long, you might want to get a bit of your side in if you were a bad boy and you suspect she might check out your story. Defensive, hateful, and vindictive are all tones you should avoid like the plague. Accepting, at peace, or at least mature are the best ways to handle what will hopefully be a brief foray into the topic.

But what happens if you find yourself in a situation where you are incredibly attracted to someone who is more than simply an acquaintance or co-worker of your ex? What if you fall for someone closer to their inner circle? Does it have a hope in hell of working?

This situation is a little more delicate as there are a lot more factors at play. Before you make a move, there are several things you would have to examine. First, how close a friend is this person to your ex? If she is very good friends with your ex, then it might not matter how long you have been broken up, it may just feel wrong to them to be pissing in a close friend’s garden, even if the weeds and crabgrass have taken it over long ago.

An important factor will be how the two of you broke up and how civil your relationship is now. If you and your ex broke up because you cheated on her, then chances are good that her friend hates your guts anyway, or at least has to pretend like she does. If your ex cheated on you, then you might get a few sympathy points right out of the gate.

If your ex still hates you, or worse, you still hate her, you might want to examine how important to you this new philly is. If they are friends, then you are going to have to make up with your ex to the point where you will be in the same room together without throwing poisonous verbal jabs at each other every 5 minutes. While your dislike might be true and pure, all this behaviour will accomplish with the potential new girlfriend is showing her that a relationship with you is going to make for a series of uncomfortable social situations, or worse, it is going to make her think that you might still have feelings for each other.

While we are on that topic, before you pursue a friend of an ex, make sure that you are not doing so in order to punish your ex. True, it would be a great coup to bed one of her good friends to show her that, not only are you so over her, you can twist that knife by proving that even her friends would choose sleeping with you over loyalty to her (come on, we’ve all fantasized about bedding the friend right after the breakup—your not alone on that one). If that is your intention, you could end up having two very angry, hurt girls on your hands that could get together to form one large super-vindictive bitch with two minds to figure out how to ruin your life forever. And you thought one ex was bad!

Once you have figured out where this new girl potentially stands in relation to your ex, try not to press anything too quickly. Ask her out for coffee, let her get to trust you a little and like you a lot before you suggest moving into a full-blown relationship. She is going to have to work out for herself if you are worth damaging, even slightly, her friendship with your ex, and that will probably take some time and effort. If you think she is worth it, treat her so well that even your ex can consider the possibility that you are not the selfish ape she remembers going out with. In fact, that is good dating advice for every girl you court.

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