Unexpected Ways Dating a Friend's Ex Can Foul Up Your Romance

Tamara McRill

So you're contemplating breaking the girl code golden rule or have already made a move towards what is often considered the worst crime a woman can inflict on her closest confidantes: dating a friend's ex. Also less commonly referred to, in this dicey circumstance, as simply falling in love. I know from experience that sometimes an innocent offer to hang out and eat spaghetti can turn into "oh, no, he's the one." I'm engaged to one of my best friend's ex-husband. You might expect a rocky road ahead for the friendship, but may be startled--and unprepared--for the issues their former coupledom brings to your shiny new relationship.

Too good for used goods

Dating a friend's ex-boyfriend or husband can complicate how you feel about your guy, but my worst issue was seeing him as used goods. Previously owned, with a racked up mileage. If you see your guy as an old beater, and yourself as just off the lot, there will be problems. Even unintentional "I'm too good for you" airs and bringing up how he got those miles will wear out the romance quickly.

Blind love can't always blast through a 'sloppy seconds' mentality and takes a lot of deep introspection on the value both of you bring to the relationship. They have moved on, you should too.

No winning when taking sides

You were your friend's ally before, during, and after the time she broke up with her ex. Naturally you took her side and fought for her cause, but now things are complicated because you feel you should also be on your man's side. You don't want your bestie to feel abandoned or your lover to feel like he is dating the enemy.

It's easy to say that the warring factions should just mutually agree to not bringing their ex drama up around you, but it can happen. Especially if there are children or pets involved. You are going to take a hit no matter which side you take, so go with how you feel--whether agreeing with one of them or stating a separate opinion.

Reminiscing gets awkward

Shared memories and jokes can solidify a relationship, but when you are dating a friend's ex, some of those good times happened while you were the third wheel. My fiance is notorious for telling me whatever must-have item I'm shopping for has been discontinued. He fools me most of the time and it always starts a "remember when you totally believed they had to stop making pore strips?" trip down memory lane. That shopping trip happened while he was married to my friend.

Even if you're not the jealous type, being reminded of a time your boyfriend was totally infatuated with your best friend can make your laughter forced--or even start an argument. It's important to focus on the shared experience and not the details of who was with whom.

Wedding party anxiety

Your best friend probably won't be in, or even at, your wedding. Let that soak in for a minute. The friend you want most to share in your big event won't be present on one of the happiest days of your life. Jane from two cubicles over may be there, but not your best friend. Talk about putting a damper on wedding planning or the urge to get hitched at all.

Even if everyone gets along famously and respects your relationship, you probably will think twice about having her in your wedding party. Do you really want him to look over your shoulder into the face of the first woman he once vowed to love and cherish or considered marrying? Of course not.

Your friend can still be part of your big day, if she wants to be. She can give valuable input on any aspects of your wedding that are important, but her ex isn't involved in, like decor or even helping you choose your dress. Like most unexpected issues that come up when dating a friend's ex, the goal is to nurture all relationships without hurting any feelings.

More from Tamara:

Guys You Should Resolve Never to Date: Unevolved Men to Avoid Dating

Crafty Valentine's Presents that Show You Love Him

Romantic Ideas for No Money Dates


Published by Tamara McRill

Tamara McRill is a freelance writer focusing on news, politics, lifestyle and business. Tamara began her career writing for newspapers, including a brief stint as a sports editor, but is now reaching lar...  View profile

3 Comments

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  • Langley Cornwell9/27/2011

    Ain't it the truth!

  • Han Van Meegerin6/29/2011

    Thank you for sharing your wisdom. Good luck.

  • Rick Soisson6/29/2011

    A useful piece.

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