Love Relationships

15 Freaky Questions To Ask Your Boyfriend

freaky questions to ask your boyfriend

Have you ever thought about freaky questions to ask your boyfriend? Sure, you have. That’s why you’re here reading this. So, now I will discover you 15 freaky questions that you can ask your boyfriend. And it’s fun. Believe me, it is!


    What is your biggest fantasy? Have you ever dreamt of ending up with a person you don’t know? Have you ever had a fantasy that someone you don’t know came to you and you just end up together? I don’t ask you, I suggest you ask your boyfriend since you’re here reading this. Funny? Sure. And the answers might surprise you.

    Have you ever been on a blind date? This one is also interesting. If you think it might be too much to ask a boyfriend things about the past, or if you simply don’t want to know, go to the next one. It will tell you more about why he likes you.

    Which part of my body do you like most? Among freaky questions to ask your boyfriend, this one is very direct and it could leave him speechless. Well, that is exactly what you wanted, isn’t it? Maybe he will be honest, maybe he won’t, but you’ll never get the answer unless you ask.

    Have you ever ended up with someone whose name you never knew? Remember the question with a fantasy? Well, this could be someone’s fantasy, but someone’s reality too. So, it’s good to check. It probably won’t change a thing between the two of you, but it could be a good thing to know if you want him to open up for you more. At the end, you can’t change what happened, and you don’t even need to. It was before the two of you. Relax.

    Can you describe your worst date ever? If you wanna put a little smile on his face, ask him this question. Ask him about his worst date ever. Freaky? It is, but it will also help the two of you connect even more. Plus, you are reading freaky questions to ask your boyfriend, and as far as I know, normal isn’t freaky at all.

    Are you okay with a relationship outside marriage? This one is not just freaky. It is also important. Why? Because this way you’ll know if you and your boyfriend share important attitudes about life. If it’s not the case, then you’re probably in a problem, or you will be in a problem later on. So, think about the future. Think about your relationship throughout the years.

    Do you want to cuddle with me? At the same time, nice and freaky. This one is good to ask if you are in the mood for that, or if you want to check out how he’s feeling about it.

    What is your weirdest habit? And what is your weirdest question – he could ask in return. Well, remind him that some questions must be freaky so you can get to know him better. Through the answers? For sure through the answers.

    What is my most annoying habit to you? Oh, this one is dangerous. Probably he won’t answer it at all. Even if he answers, ask yourself if you are ready to hear it. Well, well, maybe it’s time to remind yourself why you are reading freaky questions to ask your boyfriend.

    Make out at the cinema or on the roof under the stars? Questions that lead to one choice are always good to check if you have similar wishes and dreams. It’s not bad even if your opinion is opposite. Those questions are not of that much importance as some previous ones.

    Are you jealous when it comes to me? Imagine you’re going out with your male best friend and your boyfriend is jealous. More jealous than you can handle. He calls you all the time. He sends messages. He’s constantly trying to get you on the phone because he’s insecure about himself and it seems like he has trust issues. I know this could be really annoying to you, so you better check it before you end up in a relationship with a guy that’s not what you want in the first place. That’s why this one also goes to freaky questions to ask your boyfriend.

    Do you think that you are a good kisser? The two of you are in a fresh relationship and you’re still not sure what to think about him so you want to know him better. Great! Ask him about himself. You may not like each answer, but that’s fine. First of all, ask him if he’s a good kisser.

    What makes you feel loved? If you want him to open up for you in some more romantic ways, ask him what makes him feel loved. There is no better way to get to know him than by asking this question. Okay, this is slightly different from the other freaky questions to ask your boyfriend, but it will tell you how to get close to him, how to connect with him on some higher level.

    What do you wear when you go to bed? Interesting one. Provocative too. If he’s a shy kind of guy, maybe he won’t answer you at all, or he will try to find some way to redirect the question so you’ll be the one who will have to answer. But, besides that, what answer are you hoping to get?

    If I was with you right now, what would you do to me? One to ask before bedtime. Don’t bother if you get an answer different from what you’ve wished for, and don’t make any conclusion from the answer that you get. Probably, he won’t tell you the complete truth. Probably, he won’t be ready to open up full. Especially, if you are in a fresh relationship. Asking is up to you, the rest is up to time.

    Ready to go through this questions once again so you pick your favorites and write them down? Great idea. As you can see there is a different kind of question, but yes – those are all freaky questions to ask your boyfriend. Don’t be too hard waiting for answers. Plus that, don’t be too hard if you don’t like the answers that he gave you. Understand him too. Some of them are really dirty, while others can be too romantic if you ask a guy. At the end, you know him the best. According to these examples, try to create your own questions. Make them personal. It will show him that you care even more. Won’t it?


    About the author

    Kirsten Blackwood

    A mental health writer and advocate. Currently I write about depression. My work has always been centered around health as I previously worked at a variety of healthcare-focused agencies. I wanted to help people who were struggling with an illness or disability, but often times didn’t feel the work I was doing was providing the right voice to the people I was trying to help. Here, I can connect to you in your journey by encouraging you to share the good, the bad, and moments in-between.