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10 Questions You Wish You Could Ask Your New Boyfriend's Ex
10 Questions You Wish You Could Ask Your New Boyfriend's Ex

I never stalk anyone on social media prior to going on a date with them. I don't Google them either. There’s something to be said about meeting someone first before making a judgement, but at the same time...I do have, like, a million questions I’d like to ask the ex of the new guy I’m dating.
While I know every relationship is different, it would be nice to know what went wrong and what to expect. So here are 10 questions we all wish we could ask our new boyfriend’s ex, and why I think it would be important to ask these specific questions.
1. What made you fall in love with him?
We’ve all fallen in love with men who aren’t right for us. (Okay, maybe not all of us, and you guys are smarter than I am...) Sometimes, we fall in love with guys for the wrong reason. Because of this, it’s nice to know what makes other people drawn to him, and if people remain drawn to him over time.
2. Could he be happy on his own?
This is HUGE! While all of us want a boyfriend to call our own, you should be able to be happy by yourself. As corny as it sounds, you shouldn’t need a man to make you whole. Adapting RuPaul’s famous quote just a tad: If you can’t be happy with yourself, how the hell are you gonna be happy with someone else? Can I get an amen?
3. Did he ever lie to you and about what?
I’m not one of those people who believes you should never lie in a relationship. For one, that’s impossible. This is the real world. He will lie to you at some point or another. Whether it’s a direct lie, a white lie, or a lie by omission, he inevitably will lie. That’s how life works. But I believe there are certain things that it’s okay to lie about. Little white lies, ya know?
4. Why did you eventually break up?
Did he cheat? Did you cheat? Did work get in the way? Did he want an open relationship when you wanted a closed one? Did he take advantage of you? What’s the tea, hennnny?
5. What was the easiest part about being with him?
Relationships take work, but they shouldn’t take that much work. If you’re fighting every single day and constantly getting on each other’s nerves, then you shouldn’t be with him. So I do believe that most of a relationship should be somewhat easy. So this question is in essence asking, "How easygoing is he?"
6. What was the most difficult thing about being with him?
Does he have anger issues? Body image issues that lead to unhealthy behavior? Substance abuse issues? Trust issues? Communication issues? Daddy issues? (God I hope so!) Jesus, this list can go on and on...people are so complex and have so many damn issues.
7. What was his preferred communication?
Some people bottle everything in until exploding. Others yell at the slightest offense. Some guys just never say what’s on their mind and brood. You want to be with someone who’s open and honest about what they’re thinking and feeling. You want someone who can be vulnerable with you.
8. What type of relationship did he end up wanting?
Was he monogamous through and through? Was he open to the idea of an ethical non-monogamous relationship? Did he want to start closed, but with the notion that later down the line, once you’ve built a solid foundation, you’ll open it up?
9. Did he ever make you feel guilty for putting yourself first?
Did he ever get annoyed with you for wanting to see your friends, going to the gym, or engaging in self-care? Of course, if you’re being selfish, inconsiderate, and never including him in any activity, that’s one thing, but that’s also not what I’m talking about. I know of so many possessive boyfriends who get extremely jealous and insecure when their partner wants to do something without them. They then make them feel guilty for "leaving me alone while you go out."
10. Tell me everything about your sex life.
I mean, you’d have to be a fool to not ask this question, am I right?
How kinky? How often? How long does he last? Does he ever like to switch? Do you ever just get lazy and jerk off together instead? The list goes on and on and on...
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Zachary Zane
Zachary Zane is a writer, YouTube influencer, and activist whose work focuses on (bi)sexuality, gender, dating, relationships, and identity politics. Check out his YouTube channel here.
Zachary Zane is a writer, YouTube influencer, and activist whose work focuses on (bi)sexuality, gender, dating, relationships, and identity politics. Check out his YouTube channel here.