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. 31
    Tom Lee

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

  2. 32

    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.

  3. 33
    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.

  4. 34

    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!

  5. 35
    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.

  6. 36
    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!  

  7. 37

    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! 

  8. 38

    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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