We’ve all heard the cliché phrase, “ignorance is bliss”, but does that sentiment apply to new romances?

In my (extremely biased) opinion….

HELL TO THE YES it does! 

…and I’ll tell you why. 


During a recent text conversation with a handsome stranger, after some flirting, an inquisitive banter began. Having been out of the dating game for minute, I’ve had time to overanalyze every aspect of the courting process. So this time, rather than spew off a list of mindless inquiries, I stopped and asked myself:

What do I REALLY want to know about this boy?

I began to look back at my own experiences and think: Which questions have I asked in the past that I immediately wished I never knew the answers to?  Which  conversations have burned insecure holes into my memory and created negative perceptions of my partners?  Creating a list of answers to these questions is what led to…

A few questions to avoid asking your new boo:

“How many sex partners have you had?”


Look, we’re not in high school or any other space in time where your number of sex partners is relevant or valuable information. Numbering sex partners is completely unnecessary; unless you’re trying to break a record.

“What’s the freakiest/kinkiest/dirtiest thing you’ve ever done?”


Do NOT ask/answer this question if you intend on dating this person and are even the SLIGHTEST bit insecure. Why you ask? Because if you and this person don’t surpass or match the same level of freakiness that they did with their last partner, this insecurity will eat you alive. Not everyone can squirt or handle golden showers, so don’t give yourself/your partner that kind of pressure. Now is it okay to ask your partner which types of kink/fetish are they open to trying? Yes. However detailed accounts of how their last boyfriend took fists like a champ is information you can and should live without—especially if you’re the competitive type.

“Do you typically have a type?”


This is grade-A self sabotage—especially for insecure individuals. Asking what their type usually looks like will only have you side-eyeing everyone who fits the description; especially if you don’t. At the end of the day, no matter their “usual type”, they’ve chosen to be with you. 

“Do you think I’m hotter than you ex?”


Any question drawing a direct comparison between you and their prior partners (especially an ex)  is extremely destructive. Asking to be placed next to their past partners on a performance bar graph is demeaning and petty AF.

“How often did you and your ex have sex?”


Here we go with more unnecessary details about your boo’s ex. Rather than living in their past, try asking: “how frequently would you prefer to have sex?”

“When was the last time you had sex?”


In the past, I made the mistake of asking this while I laid cuddled up next to a guy who answered me with an unapologetic, “two nights ago.” This is a prime example of a question I wish I’d never asked. Just don’t do it.

“Did you get around when you were single?”


Anything that your boo did while they were single was fair game and is honestly none of your business. Accept them and their hoeish past or keep it moving.

“Have you ever cheated?”


A real cheater will lie anyway so why bother? No matter the context, once you hear about them cheating in the past you will find it difficult to trust them.

“Are you still in love with your ex?”


Listen, love isn’t a lightswitch that you can just turn on and off. Love fades, it evolves, and it changes over time. If your new boo truly isn’t over their ex yet, you will find out without having to ask.

Did Mario Winans have a point with his only hit, “I don’t wanna know?” Possibly. I mean, I would never invite someone to continue cheating on me like he did, but I do believe that we are better off NOT knowing every detail of our partner’s past; especially if we want to build a future with them.



Posted by:Anthony Black

One thought on “A Few Questions You Should Never Ask Your New Boo

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