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Emily Straubel

Emily is a sex and dating crusader. She founded The Red Lipstick Project as a place to talk openly about dating and sex and to connect with other intelligent women who want to find relationships that are as passionate and ambitious as they are. Emily also works with these women as a certified Holistic Health Coach to focus on their health and mindfulness as they go through breakups, job changes and other transitions to feel and look amazing in their own unique bodies. To share your story or experiences with dating in Portland email her at

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The Sex Files with Emily Straubel
Posted: September 29, 2014

Before you date your friend’s ex: 3 things to consider

dating a friends ex | Red Lipstick Project | Emily Straubel

image via Shutterstock

Everyone has had that moment – the one where your eyes lock with a gorgeous, well-dressed man across the room and you immediately connect. You spend the rest of the evening ignoring everyone else and giggling over Moscow Mules. You just met, but he feels sooooo familiar (it must be fate). Then you wake up the next morning and remember that it’s not fate. He’s familiar because you met him six months ago at your friend’s Christmas party when they were dating.

Is that a deal-breaker?

In most large cities, the dating experts come out loud and clear with a resounding “heck yes!” But living in a small city with limited options and smaller circles of smart/awesome people, it’s a much more nuanced question.

3 major factors that should inform your decision to date your friend’s ex:

Time frame

Let’s start simple with these two basic numerical questions: How long ago did your friend and mystery man date? For how long did they date?

The math might seem easy on this, but there is no perfect formula for figuring out how long a person needs to be together to form a real connection. A general rule of thumb is if they dated for six months or more, you should probably move on. That’s long enough to get beyond the surface of a flirty relationship and into the nitty gritty of real intimacy. But also, regardless of the time span, if they went on five or fewer dates, it’s unlikely they had enough time to build a meaningful relationship (read: you can go for it). These are questions you should ask your friend directly, not friends of friends or your new potential partner. While asking these sorts of questions, you’ll be able to read between the lines and learn whether they’re really okay with you going out with their ex.

How did it end?

The answers to this question are skewed because there is rarely a “good breakup”  (although I teach an online class on How to Have the Best Breakup Ever, which could fix this). The question isn’t whether it was a good or bad breakup, but how did each person react. Were they mature and civil to each other? Was it awkward at first but they got over it? Did someone cheat or lie?

Everyone gets a bit of room to be upset after a breakup, but this is where our sexual and emotional intelligence is publicly tested. If either your friend or the ex went crazy-pants after the breakup, that’s a good sign you shouldn’t move forward with the relationship. If there was a complicated cheating/lying situation, that could easily explain the breakup, or send a red flag that he isn’t as awesome as he sounds. Use your best judgement and try to be unbiased.

How important is this friendship to you?

This is the hardest question to ask yourself. The excitement of a new relationship can be blinding. At first it may seem like he’s the most important person in your life and nothing will ever come between you. But how many times have you thought that in the first few weeks of a relationship, only to realize he’s terrible in bed, he’s a jerk or worse… he’s boring.

On the other hand, how close are you to this friend? Is she a bestie? Or is she someone you see around Portland who only started cozying up to you when she realized you were potentially dating her ex? (This has happened to me more than a few times.) Be very clear on how much you value this person’s friendship. You don’t need to announce the answer to the world. Actually, keep it completely to yourself.

But here’s the brutally honest truth: I’ve seen so many people in Portland use “he dated my friend” as an excuse to avoid a fantastic relationship. I don’t want you to fall into that trap. Even now I have a close friend who refuses to date the man of her dreams because three years ago he went on a date with someone she kind of used to work with. That’s romantic procrastination – and it’s super unhealthy.

Portland is a small town and dating here can get awkward. But that’s true anywhere! You have to take uncomfortable risks to be happy. So take the time to honestly evaluate the situation and make an intelligent decision. Be conscious of your own motivations. Don’t let fear or insecurity keep you from finding a phenomenal partner. 

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