The Great Interrogation: How To Answer A Woman’s Toughest Questions

“Where do you see this going?”

If you answer with the “long run” response like marriage/kids etc. you could freak her out. (Even if it’s what she thought she wanted to hear! Women, like everyone, can be freaked out when what they thought they wanted is just handed to them.) Just say this, “All I know is that I’m really happy for you and I see no reason for this to end. I plan on staying around for a while if that’s okay.” She’ll love that last line. It will make her feel like the one in power, but not pressured.

“Are you going to sleep?”

If you are going to sleep, that’s obvious. So she’s not asking out of curiosity. If a woman asks this she either doesn’t think you spent enough time together and wants you to stay up later talking to her or, she wants to have sex, but she was hoping you’d initiate it. Your best bet is to turn around, put an arm around her and say, “I don’t have to.” She’ll give you a cue from there.

“How do I look?”

When a woman asks this, she wants you to comment on not only what she’s wearing, but something about her in particular. Women relate to their clothes: they notice how colors compliment their skin, or how certain cuts highlight their physical assets. You’ll score double points if you can say what in particular about what she’s wearing, and what she naturally looks like go together well.

“Would you mind…”

The answer is no—you don’t mind. Even if you do mind, you act regretful that you’re unable to help for x or y reason. Either that, or you jump at the chance to help. While guys are more honest with each other and will just say, “Ugh. Do I have to?” women would see that type of communication as you not caring about her.

“What do you think of my friends?”

We can break down every dynamic of our BFF’s personality and tell you why exactly she complements us and visa versa. Our friends are not just “nice” or “funny.” They are extensions of us. So when a woman asks what you think of her friends, “they were great!” won’t cut it. If you can pick up on details about them, that says to your girlfriend that you care about her. Extra points if you can say something about how she and one of her friends interact like, “You and so-and-so have an awesome dynamic. You bring out each other’s quirks.” But say something about how she relates to one of them.

“Are you busy next weekend?”

Either you are, or you’re not. Females take it much more personally if a friend says she will show up and doesn’t. Plans are more concrete in our minds. Whereas men tend to make more vague plans like, “Yeah, lets try to meet up sometime next weekend.” So, even if in your head “I don’t know” is the genuine answer because you’re going to try to squeeze in a dozen friends at a dozen unnamed times, to us “I don’t know” sounds like, “I’m free but waiting to see if something better comes along.” You either are busy, or you are not. So if you’re maybe busy, you are.

“What was your ex like?”

This one is very tricky because if you speak too fondly of your ex, your current girl will think you still have feelings for her. If you speak hatefully of her…your current girl will think you still have feelings for her. Try to strip away any emotion when talking about your ex and speak very objectively of her. “She was very social. Very into school. Athletic.” Stick to traits that are facts, more than opinion.

“What do your parents think of me?”

When a girl walks into your parent’s home she realizes she is one of many to have done so. She knows this is just another vetting process for your parents, after a long list of exes. She doesn’t just want to hear they think she’s “great!” She knows they compare her to your exes and if their review of her was something vague like “great” or “nice” she’ll think they haven’t started paying close attention to her yet. She’ll think that she wasn’t special enough to overshadow all the other girls that have walked in there. If your parents said any detail about her—any at all—say it. “My mom thought you had a great sense of style” or “My dad was impressed with your knowledge of x, y or z.”

“What do you want out of life?”

Women are known to think in more broad terms, while men are more detail oriented. It’s how we are hard wired. So, while a man may subconsciously know that he wants warmth, love, adventure and creative freedom in his life, he’ll communicate that in tangible terms like, “I want to start my own tech company that grosses X amount every year and hopefully own a home of Y size by Z age.” You know you’re not passionless and superficial, but it may come off that way to her. So, ask yourself why you want those things—what feelings they’ll bring to your life. There’s your answer.

“What’s on your mind?”

When women are silent, it’s because we are pondering on a deep matter. It could be how we’re going to resolve a fight with one of our best friends, or what we really want to do with our careers. If your answer is, “I was thinking I need to fix the sink” she’ll think you’re bored with her! Your mind has moved onto small matters! Her presence doesn’t inspire deep thought! If you really were thinking about something small, simply say, “Nothing. I’m just happy” and kiss her.

“Why do you love me?”

If you try to delve into her physical attributes and personality, you’ll dig yourself a hole. Nobody could possibly describe a woman exactly the way she wants to be described and she’ll fixate on anything that wasn’t quite what she wanted to hear. Instead, answer this question with a list of ways she makes you feel. “You make me feel confident, you make me feel safe, you make me feel so loved and understood.” You get the point. Nothing makes a woman feel more powerful than being able to instill those emotions in another human.

“What’s the douchiest thing you ever did to a girl?”

She’s asking for two reasons. The first one is a little sick: part of her wants to know that you used to sort of be a douche that played girls and felt nothing about it. She wants to hear this because that makes her the special one that made you stop your evil ways. At the same time, she wants to know that your “douchiest” wasn’t all that bad. She wants to clear her head of any terrible things you may have done while still a single guy. To be honest: some things are better left unsaid. She’ll be haunted by any crazy sexual escapades or orgies you tell her about or the time you were dating a married woman. That was pregnant. Just say, “I don’t know. I used to blow girls off a lot. Wouldn’t call them back. I just wasn’t sensitive enough.”

“Is there something that bothers you about me? You can tell me”

No you can’t. Come on. Even a man doesn’t really want to know what bothers his girlfriend about him. The only way to answer this is with unimportant answers that are also cute like, “When you wake up you look like a smurf” or “You eat all the olives out of my salad.” It’s a harmless “insult” while showing her that you pay attention to her quirks. So, really, it’s a compliment.

“So why did you love her?” (Your ex)

If you say, “I don’t know” you’ll come off as daft and un-analytical, and suddenly your girlfriend will fear that you don’t even know why you love her. You can’t say, “I didn’t” because, well, yes you did. And your girlfriend knows that. The winning answer combines a little bit of self-deprecation to yourself and compliment to your new girl. Your girlfriend wants to hear that your being with her is an indication that you’re now a better, smarter person. So, in a way, you can tell the truth. Just not the whole truth. Pick out an element of your last relationship that didn’t work for you. Say, for example, your ex really played by the rules and wanted a 9 to 5 job, and you used to want that too. Then you realized you wanted to have the freedom to be more creative and pursue your passions. That says to your new girlfriend that she inspires you to be creative and pursue your passions. See how that works?