Why You Absolutely Should Talk About Your Exes On A First Date

Five reasons to "go there" when getting to know someone new.
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Politics. Religion. Past relationships. Weird habits. Bodily functions. Marriage and kids.

These are widely seen as “taboo” topics we’re supposed to avoid on first dates to keep things low-pressure and fun, and yet, they’re some of my favorite topics to bring up on first dates.

Let me explain.

While I agree with the idea that first dates should be low-pressure and fun, that in no way means you have to purposely avoid talking about important, potentially controversial, subject matter with the person sitting across from you (or next to you, if you’re into that). I don’t know about you, but I would rather know sooner than later if a prospective romantic partner is jealous or confident, has a good sense of humor, can playfully challenge me, and knows how to respectfully disagree. In fact, the best first dates I’ve ever had—the rare first dates that got me excited for second dates—involved lengthy discussions about said taboo topics, coupled with some healthy (I repeat, healthy) debate. And let me tell you, finding yourself wrapped up in that authentic mix of flirty and straightforward conversation really ups the attraction level.

That being said, I urge you to grill your first date companions with as many taboo topics and questions as possible— just try to be playful about it. This helps you learn more quickly if you and a potential romantic partner line up in terms of values, passion, humor, and comfortability.

To take it even further, here are five specific reasons you should throw away the notion that taboo subjects should be avoided at all costs on first dates. Let’s move past this taboo talk and dig deeper when getting to know people.

1.) Big talk > small talk.

As I’ve witnessed modern technology and social media explode in popularity over the last five to 10 years, I’ve also witnessed some unfortunate side effects: too much small talk, a lack of listening skills, and purposeful avoidance of possible confrontation. Of course, real conversations are still being had and this doesn’t apply to everyone, but it’s undoubtedly gotten harder for people to truly listen and stay present. I know I’m guilty of this sometimes, so I make it a point to put my phone down and look up. The second I arrive for a date, it’s “phone down, eyes up, ears open (and heart open, too!).”

Being a firm believer in the beauty of human connection and great love, I strive to encourage others to pursue big talk over small talk and welcome discomfort in order to grow. I think it’s crucial to be with someone you can comfortably navigate through light and heavy topics with, so I try to find out as early on as possible if my core values line up with my date’s core values and if our differences are deal-breakers or things we can playfully debate over the days or months or years. To get the ball rolling when I meet someone new, I’ll lightly bring up the dullness of small talk so we can (hopefully) breeze right past it and get down to the good stuff. Taboo subjects are only taboo because they typically bring up various points of view, and people are too afraid of confrontation to dive further into conversation and healthy debate about them. Bringing up these subjects sooner than later will deepen intrigue and connection or show you there’s a lack of connection. Either way, it tells you something you need to know.

2.) You’ll make better use of your time.

One argument I’ve heard from the “no taboo subjects on first dates” crowd is: Bringing up controversial topics on a first date could turn your date off or force out differences that could end the date early. To that I say, wouldn’t you rather know right away if you and your date are able to positively deal with each other and your differences? That simply saves you time. The older you get, the more you come to know what you’re looking for, what you’re open to, and what are definite deal-breakers for you. You also tend to think of your time as more precious, so why waste it? Instead of going on three “decent” dates to figure out if the cutie from the gym or grocery store or dating app—which, let’s be honest, is where most people meet these days—is worth investing more time in, “grill” him/her on the very first date. Just remember that you can talk about serious subjects without taking yourself too seriously.

A first date shouldn’t be a total guessing game or a game of “How Interesting Can I Make Myself Look?” Of course, you’re always looking to be the most interesting, appealing version of yourself when you meet someone. That’s why it’s critical to remember that the right person will be interested in everything from your accomplishments and core values to your quirks and imperfections. So own it all, and share it all. If I’m on a date, I want to have fun and see if there’s a future. I want to know what issues matter to you, if you’re open-minded or narrow-minded, if you have a good sense of humor, what your past relationships have taught you, and if you agree that healthy couples fart in front of each other. (That last one is obviously the most important.) By covering these topics on date one, I’m able to see right away if the person I’m spending time with makes me feel comfortable enough to get real and let my walls down. If my date and I can easily move between topics together and feel comfortable and respected even when we disagree, that speaks volumes to me. On the same token, if we can’t move easily from topic to topic, that tells me just as much.

Something I like to say is, “I’m looking for marriage material, not marriage mañana (tomorrow).” I’m not looking to get married tomorrow, but I’m also not just dating for the free Cabernet and mouth-watering bread pudding (that’s obviously a plus, but I can drink wine and devour dessert on my own, thank you very much). I’m dating to eventually find the person that puts a period at the end of my sentence—and an exclamation point!—rather than a question mark. I understand that not every date is going to leave me with butterflies and that good ole “I can’t end this date without kissing you” feeling, but I want to at least try to get the most out of my time with the people I choose to go on dates with.

3.) It’s a test of confidence and humility.

Two of the most attractive qualities in any person are confidence and humility. These are must-haves for me, because they speak to a person’s likelihood of being jealous and/or unfaithful, or being a dedicated partner and calming force. When someone is genuinely confident, they’re able to build people up and positively deal with others’ emotions because they’re comfortable with their own. This is huge in relationships. It’s also a big reason I like to bring up taboo subjects.

In my experience, bringing up taboo subjects always helps me get a feel for someone’s levels of confidence and humility. I like to see how people handle themselves and if they’re able to share and listen without getting defensive, uneasy, or hostile. When a person can look me right in the eyes and welcome controversial subjects and questions with authentic excitement and assertiveness, that shows me they know who they are and they’re secure enough in who they are to avoid “playing it cool.” After all, confident individuals understand that games and facades are counterproductive to truly getting to know someone.

4.) Like it or not, exes and past relationships should be talked about.

This may sound surprising to some people, but I sincerely want to hear about a potential romantic partner’s exes and past relationships. Yes, even on a first date. This conversation doesn’t always come up on the first date, but I’m happy to discuss it if it does. Why? Because the way someone talks about their exes and past relationships speaks volumes about who they are, their capacity for healing and forgiveness, and it lets you know if they’re weighed down by any resentment or unresolved issues. I think we can all agree that this is pretty important information to have.

I’m of the school of thought that if you don’t want to talk about your past relationships or hear about someone else’s, you’re weighed down by some combination of jealousy, insecurity, and resentment. Diving into the exes talk doesn’t have to complicate everything, but it definitely will if one or both parties isn’t/aren’t secure in who they are.

The truth of the matter is, a lack of desire to hear about a potential romantic partner’s past relationships comes from a lack of confidence in oneself. If I’m dating someone, I want them to know about my past relationships, and I want to know about theirs. To me, that’s crucial in order to deeply know someone, grow with them, and develop a healthy, passionate sex life. And it can keep you from being blindsided by negative information and infidelity down the road.

5.) Give yourself permission to cut the BS, and you’ll have more fun!

I’m going to be real here: Dating can be exhausting. It’s alarming how quickly you can go from feeling excited about someone to being let down by them or your lack of connection to them. But, that’s how it goes. Sometimes you’ll meet someone and feel an utter lack of chemistry, which will keep you from wanting to be vulnerable and open up. It happens, and I completely get that.

But when it comes to people you actually feel something for, give them and yourself permission to cut the BS and really explore. Whether you know exactly what you’re looking for or not, human connection is the most incredible thing we have. You should never feel like you have to avoid certain topics in order to seem laid-back and intriguing. In today’s world of instant gratification and having a seemingly endless number of dating apps at our fingertips, it’s actually more refreshing to own who you are and be vulnerable rather than indifferent and dispassionate. Be flirty and forward and say what you feel. Ask real questions, bring up taboo subjects, and have fun. Let down that silly wall of, “This is a first date, I have to be extra cool.” There’s no need to worry about sharing too much early on because there will always be new things to share about yourself and learn about the other person. And the right person will want to learn all the nitty gritty details about you.

Now go get your grill on!

* This article was originally published on Alyssa’s blog, The Filterlyss Life. Click here for more!

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