Dating Magazine

Skeletons in the Closet: Dealing With Your Lover’s Ex(s)

By Tobehitch

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One of the hardest things to deal with when you’re dating someone is THE EX-GIRLFRIEND/EX-BOYFRIEND. This is especially true if your significant other has either an extensive dating history, or has dated someone who’s a psycho and is still being stalked by them years after the relationship is over. Kind of creepy to think that this guy/girl stalker may be watching you, from outside the window, do things with your significant other…like…play monopoly.

There are so many different elements that go into the “ex”. First and foremost, there’s the inevitable comparison that you make between yourself and the people that your significant other has dated in the past. “What was his name again?” you ask. “Bobby Valentine…” your significant other responds. WTF? Bobby Valentine? What the cuss kind of name is that? Why can’t he/she have a normal name, like Tobe Hitch. Geez. 

As soon as your girlfriend/boyfriend leaves, you jump on Facebook and SCOUR through the internet trying to find pictures of this “Bobby Valentine”. The first step in comparing yourself to your girlfriend/boyfriend’s ex is to find out what this person looks like. As soon as you see the picture, one of two things happen: #1 If the person is not that good looking (in your opinion), you start asking yourself, “why the hell did my girlfriend/boyfriend date this person”, and #2 If the person is hotter than you are, you ask yourself “why the hell did they break up?” and “do they still like each other!?”

There’s a plethora of questions that need to be answered, and the insecurity birds come chirping in your head. In many ways, one of the first obstacles that every relationship must overcome is the infamous “past dating experience” conversation. As much as the past shouldn’t matter, the reality is, there are so many insecurities that the past brings into a relationship. I mean, take me for instance. One of my ex-girlfriends “cheated” on me with her ex-boyfriend from HIGH SCHOOL, who she dated for four years in High School, and now they are married and have kids together. FML.

I facebook stalked her recently, and saw videos of their little toddler. Cute kid. Kind of depressing though. Kind of creepy on my part. Fortunately, Facebook stalking is an accepted practice in our society. Yay for Facebook. Don’t act like…you never do this…hypocrites!


So how do you deal with your significant others’ ex? Here are some things to think about as you tackle this insanely broad subject. These questions are ESPECIALLY relevant if you’re someone who doesn’t have a lot of dating experience, and are dating/are considering dating someone who has a lot of dating experience.

1. Don’t compare yourself too much with the ex (or ex’s). Look, they broke up for a reason (apparently, in the case of my ex, it wasn’t a good reason. SOB). Furthermore, she/he is dating YOU now. So even though they have history together, and that history is definitely something that elicits some jealousy, you have to keep things in perspective. IF he/she didn’t want to date you, then you wouldn’t be together. Instead of obsessing over your significant others’ ex, focus on the RELATIONSHIP that you’re committed to right now. Focusing too much on the past is only going to strain the relationship. No one likes an overly obsessive/jealous person.

2. What are you okay with? You have to answer this question pretty early. What are you OKAY with? I mean, cause, honestly, there are just some things that are…not okay. For instance, if you find out that your girlfriend/boyfriend is a guy slut/girl slut, and has slept with a ton of other guys/girls…that might be an issue for you, ESPECIALLY if you don’t have much of a dating history. Or…maybe you find out that your girlfriend/boyfriend had an “experimental” phase during their life, where they engaged in all kinds of ridiculousness…

I know that in an idealistic world, this kind of stuff shouldn’t matter…but IT REALLY DOES. And you have to answer this question. What is acceptable? What are you okay with? If you’re a jealous type, or really have a lot of insecurity issues…you may really want to think twice before dating someone who has dated a lot of people in the past.

3. How much do you like the person you’re dating right now? If you’re in love (or you think you COULD be), and you really feel like this relationships has some sturdy legs in place, then it may be worth working through any issues that pop up along the way. If the person is worth it, then the past really shouldn’t matter, especially if you believe they’ve grown and matured along the way. No one’s perfect, and everyone has a history. Being acceptable and understanding of a person’s dating history is essential for any relationship to work, and if this person is REALLY worth it, this truth is even more applicable.

4. Are they still talking? Another important question to consider is if your significant other is still talking/close to their ex. In my case, this was something that I didn’t take seriously enough. My ex-girlfriend had constantly reassured me that although she talks with her ex, that there’s nothing going on. UH. Epic Fail? The bottom line is, if your significant other is still talking to their ex and is close with them, that’s bad news. They have HISTORY together. There’s almost NO WAY that residual feelings aren’t still there. Whether they end up “making a mistake” one night because they got inebriated, or whether they just end up “falling back in love” together…if they’re still talking a lot, that’s just a pain in the ass waiting to happen. Trust me. I know.

The bottom line is this: You shouldn’t let someone’s history STOP you from dating them (unless it’s like some freaky-deeky-shiz), but at the same time, you have to approach the situation with wisdom. Don’t be stupid about it. You know yourself better than anyone else. IF something makes you uncomfortable, and is a “deal-breaker”, then call it off. If you feel like you can live with their past…then don’t let it hinder your relationship by being a constant point of argumentation. HAVE SOME self-confidence and self respect. The more the issue bothers you, the harder the relationship will be to maintain.


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