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. 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

  2. 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.

  3. 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.

  4. 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..

  5. 25

    to Selena,

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

  6. 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.

  7. 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.

  8. 28


    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.

  9. 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.

  10. 30
    Tom Lee

    You need to ready for a realionship, before you enter inot one.

  11. 31

    Just say “spoilers” and smile. Don’t worry so much. 9/10 the date won’t like you anyway and there’ll be no chemistry*, so relax and enjoy the train wreck. (35 and no relationship experience, dude, the deck is stacked so far against you, it isn’t even funny). If you want to date, work two jobs, or find a better income, spend all that money on fancier clothes and a car, and start by finding a shallow gold digger, then work your way up. Resist the temptation to give out tons of compliments or buy your date gifts in the beginning. Yes, it is shallow.
    *Unless you are a rock musician, or a CEO of something.

  12. 32
    Karl R

    Joseph said: (#32)
    “35 and no relationship experience, dude, the deck is stacked so far against you, it isn’t even funny”

    I reached 29 without any significant relationship experience. Then I had my first serious relationship and made a “surprising” discovery:
    Most of what you need to know in relationships is just common sense.

    Of course, I was pretty good at giving non-answers to certain questions. And even now (with a lot more relationship experience) I tend to avoid talking much about my past relationships. My (ex)girlfriends confided in me. I don’t break confidences. That doesn’t leave a lot to talk about.

  13. 33

    I think you’re damned if you do and you’re damned if you don’t.

    If you are too evasive about your past when asked, women will find it suspicious and think you’re a player.

    If you honestly display your relationless past women will think there must be something wrong with you.

    So I’ll go for option nr one. Loads of girls will fall for the mysterious player thing and once you’ve reeled them in it will only be a bonus that you turn out n t to be a player!

  14. 34
    Jonathan Marcus

    First, you need to work on your confidence. Confidence is very sexy to women. You need to develop an Alpha Male persona.
    When women asks you about your past relationship be honest, confidently. Say something like “I chose not to have a lot of romantic relationships or long term relationships for that matter because my focus has always been my career. But now my focus have changed”.
    I guarantee, no woman will find that statement weak. Then share what you’re now seeking.
    Do not think of or be afraid whether she’ll stop seeing you or not. If it happens so be it. Move on. When you adopt this attitude it comes through. And most of what we think of anyway rarely happens exactly that way.

  15. 35
    Leander Asischa

    ‘Be yourself’? Stick to that kinda thing is so very much of traditional but be aware that the world that we’re on today is way too much of unpredictable, not to offend but 35 and “still kinda guy”?   Well take it as a life’s trophy!   If there’s a call there’ll be a call! But if it doesn’t, then leave it! Just get on what days ahead for ya!   

  16. 36

    Really great advice here, and it applies to any/all situations where you might have a “weird dating history” and you know it might scare people off. This  advice really worked for me in a completely ironic way! I had a really rough time in my young twenties (tragic loss in the family, dating someone who turned out to be extremely abusive) so by the time I had freed myself of my major issues (and the a$$hole) I really just wanted to date a nice, normal guy. However, I knew that “nice, normal guys” probably wouldn’t be attracted to the train wreck of decisions I had made as a young adult. My first foray into dating (post-train-wreck) was a disaster…I overshared on the first date, sometimes before the first date, and both people I overshared with kinda backed off after a few weeks. So finally I decided to keep my mouth shut. I started dating  a nice guy and I didn’t ask any questions about his family until I was ready to talk about my own. I didn’t ask at all about his dating history unless I was ready to share my own.  I kept things very surface-level on the first few dates, no deep talks, etc.  The first month was dedicated to going on dates twice a week and just hanging out/getting to know each other in the moment, as people, without pasts. We had a great time, and he kept things pretty light as well.

    Turns out the guy was 30 with NO dating experience!!! After I found that out, I’d already gotten to know him over a month and I thought I had struck gold. No baggage, no issues, no emotional wounding by crazy exes, and the best part…the entire “falling in love” experience was brand new to him, so it felt brand new to me too. It was exciting seeing him experience it all for the first time. And as for my tarnished history? I was incredibly worried about sharing my past with him, especially knowing he didn’t have a lot of experience. I worried he would judge me for my decisions and think I was a bad person. But when I finally started opening up to him about my past, he just gave me a big hug and said “that was then, this is now, and from what I can tell you’re a great person.”

    So in short…keep your mouth shut the first few dates…reveal information slowly when it seems appropriate…and don’t worry about your dating past, everyone has one, and sometimes a bad dating history can be much harder to share with a new partner  than no experience at all!  

  17. 37

    I disagree with all these responses advising the poster to be vague. That’s dishonest. And asking about previous relationships is totally within the parameter of normal conversation while dating. I’ve been asked many times by men this same question and I have no problem answering it. A first date is a precursor to a second date. There are many individuals who would rather not waste time on somebody who isn’t serious. The best predictor of future behavior is past behavior. Why is it okay to ask about people’s kids and divorces but not their past relationships? We are not looking for friends or acquaintances here, we are looking for life partners and if there are dealbreakers, get them out sooner than later. There’s nothing more frustrating than finding out a dealbreaker on date 4 rather than date 1.

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