When you’re dating and trying to get to know one another, there’s a good chance he’s going to ask you all kinds of questions. How do you answer his question that seems rude, or that gives you that jolt because you have no idea how to answer.
Men can ask some pretty tough and dumb questions, right? And they can make some moves leaving us wondering ‘what the heck was he thinking?”
Instead of crossing your fingers and hoping he doesn’t ask that scary question or go in for the kiss, take a little time to prepare the grownup way in which you want to respond.
Why did you get divorced?
Why have you lived in so many places?
What you do for a living? (And you’re between gigs.)
And my personal favorite:
Why haven’t you ever been married???
Arrggh! Almost every date I had over the 30-ish years I was single asked me that freaking question! And every time, what I heard was: What is WRONG with you???” Pissed me right off.
Oh…and how about when he makes that unexpected move?
He goes in for a kiss and you are SO not ready for that.
Honestly, if he’s just an all-around rude jerk asking you a bunch of personal questions, I really don’t care how you react. Tell him he’s a creep and leave.
But if you actually LIKE the guy, how you react to something that surprises you could make the difference between you staying single…or finding grownup love.
You see, if all else is going well…he’s been respectful, he’s nice enough looking and maybe you laughed a little…you don’t want to let one moment define you…or define him!
Let’s face it: sh%t happens when two people are trying to get to know each other. You don’t want to respond in a way that totally turns off an otherwise good guy, right?
If he goes in for a kiss and you jump back in horror…that guy is going to feel embarrassed. He’s been emasculated. He’s not going to call you again.
If he asks about your past relationships and you answer with some snippy, defensive response…he’s going to assume you are a snippy and defensive woman. He’s not going to call you again.
What if he’s a good guy with partner potential who just went off (your) script for a moment?
I’ve learned that most these men really aren’t idiots. They are asking reasonable questions…perhaps indelicately. (Don’t you want to know why a 50-year old man has never married? Or why he’s been divorced twice?)
And maybe he’s trying to touch or kiss you because he’s attracted to you and has misinterpreted your signals? That doesn’t make him a horrible man that you should run from. Maybe it means you just need to have a grownup conversation.
The truth is that there are a few questions or man-moves that you can anticipate…yet you’re continuing to be caught off-guard.
Or maybe you’re not putting yourself out there, trying to avoid the questions or moves?
You think about what you’re going to wear on a date. You may think of questions you might ask him. Why not also think in advance about how you want to respond if one of these challenging situations come up?
When you are armed with honest and positive responses, you can avoid stopping a potential great date in it’s tracks. Then, steer your conversation to topics that help two good people get to know one another.
Here’s how my Prepared Statements work:
Example #1: Why did you get divorced?
You could answer: He cheated on me so I left his sorry ass.
OR you can use a Prepared Statement like this:
I’ve been divorced X years. It was a challenging marriage in a lot of ways. Maybe once we get to know each other better we can share more. For now I will say that I learned a lot, especially about how important it is that both people are willing and able to communicate feelings. I’m curious…what are your big lessons from your previous relationships?
Example #2: What haven’t you ever married?
You could answer: I just haven’t found the right guy. (And, if you’re like I was for so long, accompany that with a look that says ‘if you ask me anything else about that I’ll get up and walk out, you jerk.’)
OR you can use the Prepared Statement I finally started using:
I’ve had an enjoyable and successful career, enjoy my [hobbies] and have lovely, loving relationships with my family and friends. Now I am SO looking forward to finding a partner to share the wonderful lives we’ve created. How about you? What are you looking forward to in your future?
Have you figured out how my Prepared Statements work?
How about when he goes in for the unwanted kiss? (He isn’t grossing you out, but you definitely aren’t ready.)
You could jump back and say NOOOO WAYYYY!
OR you could take a breath, look him in the eye and say:
Bob, I’m enjoying getting to know you and would like to know more…but I’m not ready for that yet. I hope that works for you.
You tell him the truth. You set your boundary. You do it kindly, without him feeling kicked in the balls.
You check in with him and learn some very important about him. And if he’s a grownup, maybe you’ll start a grownup conversation about physicality in a relationship. (And if he’s not and keeps trying, run for the hills after calling him whatever you’d like.)
One of two things happen:
He made you feel uncomfortable, damnit!! Your fight or flight instinct kicks in. You shut down. You decide he’s a jerk. You want to punch him!
NOOO. Don’t do this!
Or you go the TMI route; sharing way too much. This almost always devolves into a bitch fest about your exes or tells him something about yourself that he ought not yet know.
Both responses are first date killers, girlfriend.
Important: You do not need to anticipate everything he might ask or might do. I’m not saying that. But you probably have those few things that give you that “Crap. I feel icky and out of control” feeling when asked or when done to you.
For me it was the ‘why haven’t you been married yet’ question. (Still makes me cringe!)
I’ve talked to scores of super smart women who have told me how much they regretted their response to a guy they wanted to see again.
Unfortunately they realize this after the date. Then it’s too late.
So, instead of crossing your fingers and hoping he doesn’t ask that scary question or go in for the kiss, take a little time to prepare the grownup way in which you want to respond.
When you do, you’ll be able to strike one more thing off your list of Why Dating Sucks. Because you see…you will be prepared with skills and information that allow you to approach dates with confidence. You can get to know the men you meet much better. You can have more fun!!
That is how set yourself up for second, third and endless dates with the right man!
So tell me…what are the questions you hate to get asked? How are you answering them or, better yet, how will you answer them now that you know how to use prepared statements?
Bobbi Palmer says:
Hi Lana, First, I’m so sorry for the loss of your husband, especially when you were so young. The way you describe this to me makes the situation understandable and I think most men would see it that way too. When you tell him is important. You don’t have to share any details right away. Here is an article to help you with when to share your “baggage.” And here is one to help with the How to share. Don’t let this hold you back from getting out there and being “real” with men. Share at the right time and remember that you don’t have to give all the gory details. Be honest but set your boundaries. Some men will be turned off and won’t want to get to know you further. But that’s okay. The right men will understand and will quickly move on to other things about you. Hugs. Bp
Lana says:
I am 47 y.o. and I was married 3 times . How to talk about this on a first date?
The first time we are very young and we find out we want different lifes.
My second husband died after 2 years marriage. (BTW He was 3 times divorced and amazing man)
The third was 3 years not drinking and all of a sudden I find out an alcoholic home, I didn’t know about his problems with alcohol in the passed and we couldn’t manage it, it ended in a disaster, the divorced was the only way for me to come back to normal life.
There is nothing to hide but I do not feel kean to open all my exs-files on a first or second date.
How to frame it nicely?
Bobbi Palmer says:
You’re so welcome, Suzy!
Suzy says:
Thank you Bobbi, in retrospect and with more experience meeting different kinds of men (most of whom are decent guys,) it’s actually funny but at the time it really threw me!
Looking at the issue from the other perspective, I actually wonder if you would consider writing a blog about how to handle it when you, the woman, actually has the difficult/potentially offensive question to ask?
There are times I still struggle with this and actually have turned down a couple of men I was interested in because I couldn’t think of a polite way to ask a question, in this case, about their personal hygiene. I know it might sound funny but on the website I use, there are several questions about hygiene and, to my absolute shock, more than a few men seem to think bathing regularly or brushing their teeth at least twice a day isn’t necessary!
Since the thought of being intimate with someone like that is disgusting to me (and I imagine most women) those men – no matter how great they sound in other ways – go immediately into the ‘no thanks’ category.
However, at times, I’ve actually wondered if perhaps they made a mistake and ticked the wrong answer. I wanted to ask but couldn’t think of a delicate enough way to put it. Again, I know this probably sounds funny, but I’ve turned down a couple of otherwise nice-sounding men because of it and really want to get a handle on it.
In any case, I’m sure there are other women who have struggled with how to ask something awkward, even if was regarding a different issue, and would probably appreciate your take on this matter as well.
In any case, thank you for everything you do – it is much appreciated.
Best, S
Bobbi Palmer says:
HI Jack. I kinda like your approach! I also believe that after the first date or two it’s time to get to the real stuff (if you haven’t already). My husband and I talked about religion and politics on our first real date. (After our meet-date.) That helped us understand very quickly that we shared our most fundamental values. I feel the same about sharing what you ultimately want in a relationship. If you are 100% clear that you want marriage, kids, etc. You don’t want to wait until date #4 to find out s/he doesn’t ultimately want the same thing. It’s important how you ask though. Interrogation doesn’t work. Your way is interesting. It’s also okay to just share what you are looking for…making sure it’s clear it’s an eventual dream; not that it’s about that particular person. Thanks for being here, jack. Bp
Jack says:
Perhaps I should have clarified my position more. I’m a 40 yr. old career army officer. I don’t online date or even have social media accounts (the powers that be consider such things a security risk). The women I’ve met and dated have all been the result of ‘real world’ street encounters in the D.C. area. My girlfriend, I met in line at the bank in November of last year. She asked me an obvious ‘break the ice’ question, I ‘picked up the ball’ and ran with it. I realize this website is geared toward people over 40, so your experiences may differ from mine. Almost all of the women I’ve dated in the last two years who were looking for a serious relationship have ranged in age from 35 to 42 or so. Almost all of them, like myself, have never been married. The women I’ve met in their mid forties, quite honestly, gave off the vibe that they were looking for fling. I’ve never been interested in flings. If the women I’ve dated have one thing in common, it’s that they’re looking for a man to marry and start a family with. Most men, I think, take off running when they start to tip-toe around the questions they really want to ask. So usually sometime around date two when I get the feeling I’m being subtlely probed, I propose a game. One deep question for another. You ask then I ask. We’ll break all the taboos. We’ve already decided we like one another. We’ve already decided there’s mutual attraction. Let’s have an adult conversation and see if we agree on the things that matter to us. I’ve fielded some questions a lot more personal than ‘do you need a man?’ So you see the question isn’t an attack at all. How she feels about a father’s role in a family is a pretty fundamental question under the circumstances. If anything my approach is a respectful one. I’m not going to waste their precious time. My girlfriend called my approach, ‘ a breath of fresh air.’ So I must have done something right.
Bobbi Palmer says:
Great advice, Suzy! Couldn’t have said it better myself. Bp
Suzy says:
In my opinion, you nailed it, with one caveat…
In my experience, you have to look at the guy as a whole – has he behaved decently and then, in a thoughtless way, as the conversation flows, asked a question off the cuff that is a bit thoughtless or even rude? Or does he come into the date with an entitled attitude and a series of pass/fail questions that he expects you to answer? You can spot the difference pretty quickly.
Personally, I’ve had both – in the first case, while I was fumbling around for an answer, the guy actually apologized and said ‘you know, that was really rude of me – it’s none of my business.’ And the date went on, he was actually a good guy.
In the second, with thr rude guy, he actually had a whole bunch of ‘philosophical’ questions prepared with which he expected me to wow him – and, no, they weren’t prepared as ice-breakers, he told me that he admired how intelligent I came across in my profile and was curious as to whether I would ‘live up’ to my profile.
I didn’t ‘perform’ very well and he made it very clear that I was, at least in terms of brains, a disappointment in person. One of questions was (I kid you not) ‘if Jesus sat down next to you right now and you could only ask him one question, what would it be?’
Anyway, now, after a bit more experience, my way is to ask myself if the guy’s rudeness seems out of character for him, based on my observations and previous dealings with him. If it does seem out of character, I would give him the benefit of the doubt (but keep my eyes open!)
But if it’s apparent that it’s part of something ‘larger’ I wouldn’t make the mistake, as I have in the past, of wasting my time with trying to be polite and appeasing. I would just get the heck out of there – life is too short and there are too many decent people out there to spend emotional currency on someone who isn’t going to appreciate it…
Suzy says:
I agree with Bobbi’s response to Jack.
I don’t mean to sound harsh but, frankly, if a man fired a question like that at me on the first date, putting me on the spot and clearly expecting me to answer the way he has determined I should respond at that moment, he would come across as very controlling (at least to me) and I would run for the hills…
Do I ‘need’ a man? No. I can survive without one and even be content. But the truth is that I am I happier in a good relationship, sharing my life. The sweetness in life comes from our relationships with others and I want to have someone to depend on, to give my love to, to take care of…and have that person feel the same way about me…
But I can tell you for a fact that I wouldn’t say anything like that to someone who ‘tested’ me on a first date…first dates are to start to get to know the person, to get a read on him/her. Not for having to prove yourself…
Sum Guy says:
Have to disagree with you Jack, or maybe need more information as I don’t want to be arguing semantics.
I don’t want a woman who needs a man, but one who wants a man. Likewise at 50 I don’t need a woman in my life, but do want and desire one. Not just a woman, but a companion.
I do get where you are coming from in that there are women who say they don’t need or want a man; and go to lengths to let you know it. Luckily I have not encountered such women in my dating as far as I know.
Sum Guy says:
As a guy, I like the answer “He cheated on me so I left his sorry ass. ” Straight, to the point, who can argue.
These questions all kind of seem like yellow flags to me, of course it can depend on the context and they may naturally arise from the conversation. I’ve gotten them from women I’ve dated, a couple will admit upfront they can be a bit like a reporter about it.
I agree with Bobbi that sex questions from a guy (when dating over 40) on the first date should put him right in the creep category.
Bobbi Palmer says:
Hi Judy, I”m glad you’re here! As far as getting to know him in a deeper way, the best way to do that is to share in a deeper way. Show him you are interesting in, and willing to share a deeper part of yourself and you life. If he is willing and able, he will follow along. If not, that gives you an indication of if he is ready to get close to another woman. Don’t be afraid to have direct, grownup conversations with him. And as far as age…who really cares at this point in life? My husband is 9 years older. I love him and we have a great life. Right now, that’s all I need to know. Best to you, and keep learning with me. I’m rooting for you!!! Bp
Judy says:
Bobbie, What a help your advice is to this 55 yr old dater. On the subject of “what not to ask” and “getting to know you” questions, my situation is a bit different but in the same subject realm.
I’ve been divorced 5 yrs and have limited dating experience. I am guilty of deciding up front whether the person is one I would consider spending the rest of my life with – I don’t date just to date. So……I started seeing an absolutely wonderful man about 2 months ago. We enjoy each other’s company and companionship greatly. His wife passed away 8 months ago.
My concern – we have not yet had in depth “getting to know you” conversations about our lives. Our time is spent with companionship and enjoying being with someone we feel comfortable with. – this is wonderful but I can’t help but feel it is time to have some in depth talks. I recognize that he is somewhere between still grieving the loss of his wife and wanting to move on with his life. I do not want to push him past his comfort level while he is dealing with this but wonder if and when I need to initiate the talks.
Let me say that we have known each other (and our families) as friends for years. So on a certain level we know each other’s character and basic personal stories. We already respect and admire each other and that is invaluable. I could see this relationship turning into a commitment in the future but I feel I am making this determination without all the facts and am not willing to jump all in and begin to release my heart until we’ve had the talks.
Another topic – he is 10 yrs older than me. What if any concerns should I have with that?
I must say I was believing there were no good men – I. WAS. WRONG!! I want to do this relationship right… from the start. I recognize it is a treasure…..
TooSmart says:
I mean of course “Why would you further want to know someone who makes me feel Uncomfortable on date number 1?”
TooSmart says:
Noquay, I find the “Why didn’t you have kids?” question very rude. Imagine when this question is asked to a woman with fertility issues. I feel that people with kids feel entitled to ask this question but do we childless women ever ask someone “Why did you have kids?” I don’t think so.
I have no problem to answer the question why I don’t have kids (very simple: did not find a good partner during the years when it was biologically possible for me to become a mother and did not want to raise children by myself) but not if it is fired at me during a first date. It is a very personal question which I only want to elaborate on if a certain trust is established between me and the other person.
Timing is very important in dating. Someone who has his/her timing right is very attractive, I think a lot of people forget that.
TooSmart says:
Jack, it does not seem mature to me to let your opinion about a woman depend on her answer on one question, and one which is almost an attack. “No” seems to be the obvious answer to the question since the woman you meet is single and has still managed to accomplish things: a job, a social circle, a house, etc… If we would need a man we would be very sad creatures because it would mean we can’t achieve anything unless we have a man so no, we don’t need a man.
You might ask if a woman would like to have a man in her life, would like to have a partner, husband and you will get another answer. But if you insist to submit a date to a “litmus test” don’t be surprised some of your dates will be turned off by you.
TooSmart says:
I think it is incredibly rude to ambush your date with such indiscrete questions when you just met each other. Whether it is a man or a woman (yes I am sure some women do the same) it shows a lack of empathy and a judgemental attitude. When we are over 40 and single we know how relationships can start very promising but can turn into a big disappointment some years later, we know how difficult it is to find that one person with who a good relationship is possible so no one is better than the other, we are all in the same boat. If despite this someone still approaches his/her date from a superior position in which he/she feels she can question her/him and judge, it shows an unpleasant character and this will resurface if you have a relationship with this person.
I personally do not see the reason to put up a brave face in such a situation. I mean, why would you try to save the date if someone behaves like that? I think we should expect a minimum of manners from our dates. So I would in all honesty say that the questions makes me very uncomfortable because it comes way too early in the process of getting to know each other, and I would just leave. Why would you further want to know someone who makes me feel comfortable on date number 1? If you can’t even do your best at that moment, then when will you do it?
I also feel that the suggested answers sound like apologies in some way and I don’t think anyone should apologize for having had a life, with successes and failures.
Bobbi Palmer says:
Happy to help Allyson! Yah, sometimes they are a creep. And sometimes they are just nice guys asking a stupid question! Be sure to consider all you know about him before you make a judgement. Qualifier: any question about sex on first date goes right to creep category. Glad you’re here!!! Bp
Allyson says:
I love this — so helpful! I’ve tried scripting and memorizing responses to “challenging” questions men seem to like to ask on the first date, but they’ve never been exactly right. The three-part formula is brilliant — and it flips the question-answering onto the man in a good way.
In addition to the question Nancy gave above, I’ve been asked: Why did you get divorced? What was your relationship with your ex like (also, what did your ex do wrong)? How clean do you keep your house? How much debt do you have? Would you have sex on a first date? How soon are you willing to have sex? What are your sexual preferences? Are you the jealous type? and How much money do you make?
Many of these fall into “Tell him he’s a creep and leave!” territory — it is so freeing (and awesome) to hear that from a dating coach!
You rock!
Bobbi Palmer says:
Yes, I agree with what you said about all the propaganda. However, the truth is that it has affected many of us – men and women – and it takes time to let go of old truths. I know the women here are heartily working on it. But you’re still going to scare them away with that question. Of course you are free to do as you wish, but I think that your “Test” is going to keep you single OR attached to a woman who truly is needy and has low self esteem.
If you want to attract a confident, accomplished, smart woman…I highly recommend you reframe, my friend. Digging in on this may not serve you well.
And btw Jack…send me an email at bobbip at datelikeagrownup.com. If you’re open I’d like to ask you a question. Again, glad you’re here!
Jack says:
I have thought about ‘sugar coating’ the question and decided against it. It’s a ‘litmus test’ question. Does she have the emotional maturity to admit she does ‘need’ a man, in the face of overwhelming propaganda to the contrary? Before anyone gets upset at the use of the word ‘ propaganda ‘, you should know that there is just as much if not more propaganda coming at me from male sources, telling me to avoid relationships and ‘use and discard’. Frankly, I’m sick of it. I’m tired of playing playing the game of ‘he or she who cares the least wins’. Make no mistake, it is propaganda used in a war of the sexes that has no winners only losers and a whole lot of casualties.
Bobbi Palmer says:
Oh Jack…what a helpful comment! Yes, I get it. Just know that we “women of a certain age” have had so much thrown at us from the women’s movement that tells us that neeeeding a man is for losers. We DO need you…it’s just sometimes hard to use that word. Would you reframe your question? Maybe ask ‘Where do you see a man and relationship fitting into your life?” It’s just that NEED word. Does that make sense?
And ladies, please read what he says! It’s not a bad thing to need a man…it’s lovely.
Thanks Jack. Glad you’re here. Bp
Jack says:
The question I always ask, that’s thrown more than one woman off her game, is, “Do you need a man?”. The knee jerk reaction is ‘no’. That’s the wrong answer to me and strike one against her. I’m not interested in being an accessory. I want to be with a woman who needs me every bit as much as I need her. I’m not talking about wifey at home in the kitchen financially dependent circa 1955 nonsense. I’m talking about love and emotional connection. A woman who needs me for those things is infinitely more attractive to me than one who merely wants me for those things. Usually, I get a ‘deer in the headlights’ look from women when I ask that question.
Bobbi Palmer says:
Perfect, Nancy!!! You GO!!!
Noquay says:
Some of my least favorite questions:
1. Tell me about your family. I came from two abusive family situations, Got out, got an education. Sadly, as of two years ago, they’re all deceased.
2. Why didn’t you have kids? I was a de facto parent to a sibling starting at 17, at 56, I’m done parenting for good. Need more reasons? See #1
I don’t actually give those answers though they’re the truth. Do wish folks wouldn’t ask.
nancy says:
The question I often get asked is how long have you been on this dating site and what have been your experiences?
I now will answer that question by saying, You know what, Bob, I have a wonderful life with a great career and family and friends and now I am really enjoying meeting new people so that I can find someone to share my life with. This dating site is just one way for me to get out there. I would really like to get to know you, Bob. Tell me, (and they I would ask him a question to get to know him better).