I’m a 35-Year-Old-Guy with No Relationship Experience. How Do I Let Women Know?

I'm over 35 and dating. One question I get asked a lot is about my past relationships.

The problem is, I haven't had any.

I've had one problem or head trip after another. I've also been a loner and a bit of nerd. I can honestly say that I am over all of that.

I know these women are asking me this question to screen me out, the way an employer would look at past work experience.

I know I am a sane, well-balanced guy who will be considerate, but I am afraid that if I am truthful before I get to know a woman I will get dumped by the second date.

Any advice on how to handle this question?


Dear Robert,

Among the most common advice given by relationship experts is this doozy:

“Just be yourself!”

Tell that to the guy who asks a first date if she likes anal sex. Or the woman who complains that all men are pigs before she’s even ordered her Caesar salad.

Encouraging these folks to be themselves is a crime against humanity. They’d be far more successful on dates if they were to try to be anybody else. Of course, these people never learn from their mistakes, since they never get any feedback. When others don’t return their calls, they assume that it’s the other person’s loss, and tell themselves others are crazy for not appreciating their “honesty” and “directness”.

“Hey, I’m just being MYSELF here. You don’t expect me to just LIE, do you?”

Uh, if not telling her that she looks fatter than her photo is a lie, then, yeah, lying’s not a bad idea.

Which is just a long way of saying, Robert, that full disclosure isn’t always the best idea. Listen, I’m not one to make dating sound like a series of job interviews, but if you think of each “interview” as a chance to make a strong first impression, you don’t go into an all-out confessional.

“Yeah, see that line on my resume that shows that I was employed at NorthStar Research in April ’97? That’s because my boss was a dick, who caught me surfing for porn during a sexual harassment training session. Plus, the job really sucked because he was always asking me to do stuff for him…. My greatest weakness? Probably that I’m lazy. And a stoner. A lazy stoner.”

This is not how to interview. We know this. But it doesn’t stop us from telling the whole truth on a date under the guise of “full disclosure”.

Dating has always been a perfect example of “don’t ask, don’t tell” and I’m always amazed when not everyone has read that same rulebook.

Dating has always been a perfect example of “don’t ask, don’t tell” and I’m always amazed when not everyone has read that same rulebook. Like when you go out with someone who says that she’s got another date tomorrow night. What good could POSSIBLY come out of me knowing that right now? Well, in her mind, she’s just telling the truth, letting me know that she’s got other options, perhaps informing me that she’s not that interested. But chances are, she’s not sending a message. She’s just being STUPID….

And that’s what over-sharing is on a first date. You take Wellbutrin to keep it together? Save it. Your last boyfriend physically abused you? Save it. You just got out of rehab? Save it. In other words, if you think it might be poorly received, SAVE IT for later. Because we’re all a lot more forgiving of “issues” when we know and like someone than when we’re meeting them cold on a blind date. The same thing that might label you a “freak” on date one may actually be heartwarming and vulnerable later on.

By the way, I say this as a guy who has some legitimate “issues” himself, and never ran into major troubles with any women because of how and when I dealt with them.

SO… are you going to be asked about your relationship history frequently on dates? Absolutely. It’s a fair question, and usually a very revealing one. But if you’re not ready to reveal, try gliding past it. And please, keep it light. Being matter of fact is key, since the bigger deal you make of it, the bigger deal it becomes.


“So what happened with your last girlfriend?”


“Sorry, previous relationships are a date 3 question. Unless we’re talking about yours, of course…”

“Let’s just say that I haven’t had anything serious in a really long time.”

“I’ve been so focused on work for the past few years that I haven’t left much time to date. Which is why I’m here with you right now.” 

Like a politician, you can answer the question without really answering the question.  


Again, I’m just making stuff up here, but, like a politician, you can answer the question without really answering the question. The only way this backfires is if she turns into a pitbull and presses you for a more tangible answer, names, dates, hair samples.

Of course, if she does interrogate you, you probably don’t want to go out with her anyway.

Join our conversation (44 Comments).
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  1. 1


    I had a slightly hectic morning and the first paragraph of your answer gave me a GOOD laugh. Thank you!

  2. 2

    I very much agree with your advice here, Evan. I don’t push others for personal details, but I know I tend to impart tmi sometimes – I think I do it because I somehow feel if they are going to decide you aren’t for them, you’d rather be left sooner than later. I do have a question for you and everyone out there – or maybe, just stating what I think and wondering if others think so too …

    Isn’t a date asking you about your past relationships on a first date, particularly if question is very specific or persistent, sort of in the same league as Full Disclosure from the get-go? I.e, a no-no. Seems like that is bad form on the askers part and something she (or he, as I have had that question tossed to me from square one by a couple of guys in the past also) should be saving for later as well?

  3. 3

    Great advice from Evan.

    I don’t much care for the previous relationship interogation on first dates either–giving or receiving. “Do you have children? ” is appropriate, but details beyond that are not. Surely people can come up with other topics of conversation to get to know each other than detailed relationship resumes?

    And consider this: Anyone who’s on a date past age 18, and not a widow/er can honestly say about themselves, “I haven’t found the right person. ” “Yet.”

  4. 4

    The question of past relationships is an important one for us women, because nothing sucks more than falling for a guy, who later decides he’s just not ready for a relationship…or just isn’t a “relationship type person…is really just a loner.”
    Been there…done that, and had my heart broken.
    So men…before you start looking for a relationship…KNOW that you really want one.

    1. 4.1
      Donnie Reiter

      That’s a stupid question to ask a guy on a first date because that’s like asking may I have your checking account on a first date please . who asked that ??????

    2. 4.2

      I don’t know what you mean by “us women”. I’m a woman and have little to no interest to talk about previous relationships; they are in the past for a reason. Once you’re getting to exclusivity and you know one another then yeah, go ahead and ask. But my past relationships are in the past and I’ve learned my lessons and it has nothing to do with the current relationship (except that I won’t repeat things I found didn’t work again!)

      1. 4.2.1
        Adam ishaq

        I like this response as a guy all I care for is woman I’m with and tomorrow.

  5. 5

    Good advice, though I’d like to point out that there’s a difference from being yourself and being polished/refined/classy. Being yourself means not trying to be something or someone you’re not otherwise you’ll come across as phoney. The other has to do with behaviour.

  6. 6

    Evan’s exactly right here. You need to learn how to give the classic non-answer answer. Let your date get more comfortable with you before you drop something like that on them.

  7. 7

    I think this advice could put the guy on the right track as long as the “story” he comes up with feels comfortable to him. Cuz if you feel like you have something major to hide and it gets awkward that could be.. awkward. I agree you could be straightforward while de-emphasizing the past adn refocusing on the date at hand. I would be more put off by later finding out a guy misled me (lied) than the fact he has not dated. In fact I have no problem dating guys who have not dated much…

  8. 8

    It’s not lying, it’s flirting. (credit Mystery)
    You’re not being dodgy, you’re being playful.

    Neither of you has earned the right to play 20 questions on the first date. Keeps things flirty, fun, light, playful, sexy, and avoid all closets full of skeletons. If she asks about prior relationships (or lack thereof), simply dodge, as Evan suggested above. Those are good btw, I’m going to lift them.

    Also, project confidence and rock solid cool. YOU should be the one screening her, not the other way around. If she tests you in this way, simply be clever. Make sure you direct the flow of conversation. Flirt at all times. The first date is NOT really about getting to know each other, rather it’s about being fun and unique.

    If you make it to date 2,3,4 etc, then you’ll have to start getting into details. By this time, you should have established yourself as a fun, cool, sexy beast and that’ll trump most if not all skeletons.

    1. 8.1

      Interesting. I have found that unless you are immediately 100% comfortable with the other person it isn’t worth pursuing. The people you feel immediately at ease with are the ones to see again. The ones you need to strategically ask and answer questions around are not the ones to waste time on.

  9. 9

    I clicked on this one just to see how Evan was going to respond and as expected, he is right on!! I am a 45 yr old divorced woman who has been dating for the last three years after a 22yr marriage. When first dating, I did have certain criteria that if the man shared, I would be done with him. And he sure better be honest up front about all. Well, I have learned to be more gentle and understanding. And as long as he seems like a good guy and my intuition is not bothering me, I continue to go forward and get to know the person. Now I have looked past many things that I never would have in the beginning. And it’s because I stopped grilling the guy on the first few dates and gotten to know him as a person. A good person will learn from their prior mistakes, so it’s unfair to judge them on their past. My current and first serious boyfriend since my divorce, did not disclose several things about himself until after I knew him well and was in love. I was OK with all of it because of the way he told me and how he told me. He did the right thing for our relationship. If I would have known these things upfront, I don’t think I would have moved past the first few dates. So Robert I would follow Evan’s advice and actually practice some of your responses to those certain questions concerning prior relationships. If you are very successful in your career, I would do what Evan suggested; “You have dated casually but your career was more of your focus and you are realizing that now you want to put as much energy into finding the right woman for you!!” Something along those lines….good luck and most important….BE YOURSELF and BE FUN!!!

  10. 10

    J wrote:
    Isn’t a date asking you about your past relationships on a first date, particularly if question is very specific or persistent, sort of in the same league as Full Disclosure from the get-go?

    I think it is at the least ironic since complaints about dates going on about their ex or other baggage is almost a cliche

  11. 11

    Lisa Jan 31st 2008 at 01:43 pm 4
    The question of past relationships is an important one for us women, because nothing sucks more than falling for a guy, who later decides he’s just not ready for a relationship or just isn’t a relationship type person is really just a loner.
    Been there done that, and had my heart broken.
    So men before you start looking for a relationship KNOW that you really want one.

    I agree with the reasoning and I agree with why women ask this question. If people are still single past a certain age there is a reason why and usually it is not an endearing one.

    However, there are some freaks out there who actually do improve themselves and become more of a catch as they age. Older women do seem to be ready to try and convict a guy without a trial.

  12. 12

    Think Lance’s post is apropos for both men and women, and certainly for Robert. It works for me at any rate.

  13. 13

    Hi Robert : )

    When all is said and done, quality is still more important and more valuable, than quantity.

    Though still agree with Evan and the others that you be yourself, don’t disclose too soon (thereby possibly shooting yourself in the foot – very true for any of us that tell some things too soon, including me), and find the positives in who you are and what you have accomplished and become. Even, in what you haven’t done – like not having LTR.

    For example:
    Maybe you also have something of an advantage in that you don’t bring a lot of prior relationship baggage to the table?

    Best of luck to you! J

  14. 15

    to Robert,

    …you are asking questions about the female species and behaviour, which I commend you for, and I encourage you to continue asking, go to single seminars, etc….(most men don’t know what they are doing, and we don’t ask)…….there are people with answers, that you want to hear, they are far and few, just keep asking……

    I believe relationships, for a man, are about being consciously aware,..about being informed,..

  15. 16

    I enjoyed Evan’s response to this one. Well written and to the point.

    Lisa said that the reason women need to ask questions is because they need to know certain things in advance, such as if a man is afraid of long term relationships. That way, a woman could avoid spending time on someone who is afraid of commitment. I can certainly empathize with that.

    However, let’s say a man just wants to date several women at once, and has no interest in a LTR. If that man was asked about his intentions on a first date, he is likely going to avoid a direct answer, change the subject, or lie.

    Men know most women want to hear that a man is interested in a long term relationship. Therefore, if he is interested in having the woman’s phone number as one option to call when he needs sex, he is going to make a LTR look like a possibility just to keep her interested. Telling her the honest truth such as “No, I find you attractive and would enjoy sleeping with you, but, I wouldn’t marry you. I’d like to be able to phone you for sex, should my other partners be unavailable, and hopefully you’ll be available upon short notice and make no further demands on my time.” How many women would be keen on that arrangement?

    Or, the man will answer in vague terms such as “some day” he would like to settle down. The overly hopeful woman will read that as meaning with her. He only means that, yes, theoretically “some day” he’d like to settle down, but not necessarily with her.

    I think it is better to carefully observe a man’s actions to try to find out his plans. Asking a direct question doesn’t guarantee that he’ll be truthful. Sure, men want to be truthful when they can, but sex is a powerful motivation to lie or stretch the truth. Although some men are honest about it, most men who want to get sex or companionship without strings attached know it is easier to be vague about their intentions, or outright lie.

  16. 17

    to robert,

    …women are constantly testing, you, they will find out what they want to know…

    1. 17.1

      She will find out and end it so quickly.

  17. 18

    to Li-Ann,

    …a woman’s mind is built to follow a man…and I know women find this very frustrating….little do men know, that, we don’t have to lie, and, most of the time, we will still get our needs met. There are women, who think they can handle this situation….

  18. 19

    Li-Ann, you are so right. I’ve met quite a few men doing exactly what you describe. Even men tell me that “men are dogs.” They’ll lie or lead you on just for sex.
    Unfortunately sometimes its difficult to figure out who is for real, that they’re genuinely interested in me, or they’re just trying to get laid.
    But my latest relationship was going great until he decided out of the blue that he just didn’t want a relationship. And he truly hasn’t dated anyone since me. He said he thought he wanted a relationship, but found out he really didn’t want one. Some guys really don’t need companionship, sex, love. They can live without it. Not me, and it killed me that he could just end our relationship just like that.
    So I’d be VERY skeptical to date anyone like Robert, who has lived just fine all these yrs without a LTR. Sorry Robert, I wouldn’t believe you.

  19. 20

    to lIsa,

    ..you are so right!….women that have been hurt, runover, used, abused, just recently out of a bad relationship,.., will not get into a LTR….some run from men, others get into the church activities, others, grandma it out….

  20. 21

    To Hunter

    grandma it out… Funny expression.

    But so true…my sister at 37 totally gave up on men and quit dating…for years now. She didn’t need a man.
    Me…I’ve been abused, in a bad relationship but I haven’t given up on men. I know there’s still some good ones out there.
    I just haven’t found the good one that wants a LTR.
    In my 40’s I’m beginning to think it’s like looking for a unicorn. lol

  21. 22

    Lisa, on the behalf of men like Robert, did it ever occur to you that you can get just as dumped by a man who has been in several LTRs ( I *love* these acronyms BTW ), who wants an LTR, who starts an LTR with you and then like in the situation you described, stops the LTR on a dime after he decides being with you isn’t for him?

    I’m not coming down on you, I would be tempted to do what you are doing if I had your experience. Every once in a while I have a conversation like this with a girl-friend, but for the most part I never get to hear a woman’s thought process in matters like these.

  22. 23

    I’m bemused by this notion of ‘starting’ a LTR and how you can decide this upon first dating. Seriously, how do you know you will even LIKE each other after a couple months? Let alone have fallen in love, found yourselves amicably compatible in everything important to each of you, and in total sync about your future together?

    The purpose of DATING is to get to know each other and see where it goes. Sometimes the relationship turns out to be long term. Sometimes it doesn’t. And I know of no way of predicting which it’s going to be right in the beginning.

    If you want to try to avoid involvement with someone who is just out for sex: DON’T SLEEP WITH THEM UNTIL YOU GET TO KNOW THEM FAIRLY WELL. And certainly, talk about, and come to the mutual agreement to be exclusive BEFORE taking your clothes off.

    I believe many of these ‘love ’em and leave ’em’ scerarios are the result of assumptions. Assuming someone wants a serious relationship with you because that’s what you want with them. Assuming that sex makes you a couple, when in fact it may just mean that you are two people who had sex together and that’s it.

    Asking questions is fine up to a point–but really, only time will tell if the relationship is going to last beyond the initial courtship phase.

  23. 24

    to lisa,

    “grandma it out,” some women would much rather spend time with their grandkids, because they say, that, warmth from their grand kids is priceless…which is true, men can’t compete with that..

  24. 25

    to Selena,

    ..doesn’t the average woman know her partner fairly well after the 3rd date?….

  25. 26


    I get to know someone well, and date for awhile before deciding if we want to be exclusive, which would hopefully turn into a LTR. I don’t just meet someone and say do you want a LTR with me? lol
    But I only date people who want to find a life partner.
    I’m not at all into serial daters or those looking for intimate encounters.
    But like I said I had a great relationship with someone who just out of the blue decided he didn’t want a relationship after all. Broke my heart.
    So I’m much more cautious now.
    Steve, To answer your question…yes, I know you can just as easily get dumped by a guy who says he wants a LTR….from experience….see my previous post.

    My thing is, I’m 43 yrs old, had a bad marriage that I stayed in way too long, and I want to find a great, wonderful relationship. I just don’t want the heartache that goes along with looking for the one. So I wouldn’t date someone who had never been married or had LTR’s before. There’s obviously something going on with them that they can’t settle down with one person.
    My favorite type of guys are real family men, who love their kids, who loved being married, it just didn’t work out.

    1. 26.1

      In other words they are losers.

  26. 27

    To hunter:
    Actually, unless the two people knew each other fairly well PRIOR to dating, I don’t think they know each other fairly well by the third date. The average woman might persuade herself she does know the guy fairly well though, if she wants to sleep with him. Then she’s hurt/disappointed when he subsequently does a fade out, abruptly disappears, or simply decides he doesn’t want a relationship with her. Getting to know him better, longer, before sex may clue her in to what he’s really all about and how he really feels about HER.

    To Lisa:
    I empathize with you. I’m also in my 40’s and would like to find someone to have a relationship with that is more than casual dating. Thing is though, we could theoretically meet any number of men who professed to want the same thing, yet turn out NOT to be the one for us. Or who found us NOT to be the one for them. Or with whom we each found the frequent concessions and compromises involved maintaining the relationship became not worth the effort. So despite what we say we want, LTR just doesn’t happen.

    You may think you’re avoiding potential pitfalls by not getting involved with someone who’s never been married or had a LTR, but obviously for those who have had that and are currently single, it means they couldn’t sustain those relationships for whatever reasons. And those same reasons could be telling as far as how any new relationships might go. Or they may not at all.

    I don’t see anything wrong with only dating people who say they want a life partner as long as you recognize that only time will tell if it works out that way–and that’s something you simply can’t predict despite your screening process.

    Sorry about your broken heart Lisa, but it sounds as if your beau recognized he just wasn’t cut out to be your partner for life. And if he felt that way, he probably would not have been a good one for you if he had stayed. Perhaps he did you a favor even though it doesn’t feel that way now.

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    Probably the same island I’ve been on. I am VERY painfully shy, and it is oppressive. I can imagine EXACTLY what this man is going through (though I am a woman). I find it very easy to converse with men I do not find attractive, but my throat clamps shut and goes dry and my palms sweat and I actually feel physically faint if a guy I am attracted to makes even the slightest move to speak to me (and yes there is one in the office where I work at the moment: and I want like CRAZY to date him but my knee-jerk shyness response is to clam up when he tries to approach me — I’m 99% certain he likes me too, and he seems to have told most of the people in my department that he likes me, but they aren’t allowed to tell me – I’m just overhearing bits of phone conversations over the next cubicle and I’m putting two and two together). I am 39 and have never been in a relationship either. My longest psuedo-relationship was when I dated a creepy engineer (whom I met on match.com) with a drooling problem for about 3 months, 5 years ago, but I don’t count that as a “relationship” since it consisted of about 4 or 5 dinner-movie dates (and he was stone dead quiet – no conversation!!) and one very blah makeout session fully clothed (during which the drooling became a major turnoff issue), after which I didn’t call him again, and he only emailed me once (6 weeks later) to find out why I didn’t call (!!!). But back to my story. This shyness problem was a serious issue in college (during which time I fell head over heels for a guy, but wasn’t EVER able to speak to him! How pathetic is that!), and most dates I have been on were one-date wonders – with men I found nice and pleasant, but wasn’t attracted to. I think men know when you don’t find them attractive and there’s no chemistry, because no matter how polite and nice to them I am, they never ask me out on a second date. I’ve decided the shyness problem is an overwhelmingly negative behavioral issue that is seriously affecting my quality of life. It is a conditioned response to something that must have happened to me in my childhood. I don’t control it; it definitely controls me. I want to resolve it quickly and effectively, so I have started doing hypnotherapy to overcome my shyness, to feel more confident and relaxed around men and so on. I am certain I am not the only painfully shy single person out there (I’m also certain a lot of people are dating online, b/c they also can’t cut it socially in the real world for whatever reason). We need help changing our conditioned responses in social situations, not further criticism that makes us feel even more incompetent and reinforces the negative messages we are ALREADY telling ourselves (believe me).

    As to what the guy should say, I find it’s best to tell people “it’s been so long I feel like a virgin all over again” (cue laughter) or “no relationship worth remembering, and life’s too short to dwell on past disappointments” (does that sound upbeat enough?).

    Really, this guy’s problem is not what to say, but how to feel better about himself – how to feel competent at dating and relationships. That’s not something you can ridicule someone into feeling. It takes therapy. Personally, I don’t have years and bottomless income to waste on psychotherapy, so I choose hypnosis, which is cost-effective and fast: it’s giving me some quick results already. I recommend it to other singles on this board as well as the guy in the story.

  30. 29
    Michael Ejercito


    There are a few things you should disclose, like whether you have been married before and whether you have had kids and the general vicinity you live in. (Obviously from your post, you were never married.)

    If you are asked further details, such as if you have ever had any sort of relationship other than a marriage, or your address, tell them that you do not want to answer until you feel you can trust them.

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