ASK SEAN: "I'm scared to tell my new boyfriend how many guys I've slept with."

When it comes to figuring out men, it sometimes pays to skip the girl talk and head straight to the source. This column is my advice on your most burning questions about guys. And since I’m gay, I’m kind of halfway inside your head already. Let’s dive in!

This week, you asked:

“I’ve slept with and dated way more guys than my new boyfriend. He’s really open with talking about exes and his “number”, but I’m scared to tell him about my past, which includes sleeping with more than 40 guys, in case he judges me for it. What should I do?”

Relationships require honesty. But they do not, in my “professional” opinion, require full disclosure.

If you want your relationship to last, then you should never lie to your partner. But it’s your right, especially when you’re in a new relationship, to keep some aspects of your past private. Your job is to figure out a way to communicates your past while effectively expressing your desire to keep some parts of it private.

A blunt line like, “I’m not keen on opening up our ex-files this early on” should do the job. You can also be a bit bolder and say, “I’ve been in many more relationships than you, so my number is higher. Let’s leave it at that, please.” That should end the conversation.

Learning to articulate your boundaries with a new partner is an important milestone to work through. Testing these types of lines out with him will help you learn a lot about your long-term compatibility.

All that said, I want to make one thing very clear. If your relationship lasts past the “new boyfriend” phase, it’s going to be difficult to keep your history a secret. It’s not impossible, but it’s also highly unlikely. He will work out, through your stories or random run-ins, that you’ve dated quite a few more people than he has.

The truth, as is often the case, will come out.

Ask yourself: would you really want to date a guy that doesn’t love you for who you are? Or in this case, who you once were?

There’s nothing, repeat, nothing to be ashamed of for having sex with multiple men. Don’t let society tell you that women aren’t allowed to explore their sexuality in a consensual and enjoyable manner.

I firmly believe that this is your decision to make. But I also know with every inch of my being that your past is nothing to be ashamed of.

If you believe this too and decide to have an honest conversation with him, treat the talk like it’s no big deal. He will feed off your energy, so take control with a calm and unapologetic attitude. If he flips out, then he isn’t the right guy for you.

Add him to your “list” and move on. You’ll date a guy who will not only find your past to be appropriate, but really sexy. I promise you that.

Read more from Ask Sean: 

• Ask Sean: “My boyfriend and I have regular sex, but frankly it’s… really boring.”
• Ask Sean: “My boyfriend won’t stop liking photos of random girls in bikinis.”
• Ask Sean: “My ex is getting married and I feel… weird about it.”
• Ask Sean: “I’ve been with my boyfriend for three years. Now he doesn’t want to have sex.”
• Ask Sean: “I’m fantasising about my boyfriend’s brother. Is this a bad sign?”
• Ask Sean: “My boyfriend poops in front of me all the time. Is he too comfortable around me?”
• Ask Sean: “I was on my boyfriend’s computer when I discovered he might have a… fetish.”

Sean Szeps is a freelancer, and Mamamia’s resident Agony Uncle. To ask him a question, you can email submissions@mamamia.com.au. You can also follow Sean on Instagram, or listen to him on Mamamia’s parenting podcast, The Baby Bubble. 

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