Question: How Far Into A New Relationship Should I Start Having Sex?


I’m an 18 year old female and I’m looking for your “older guy” advice… I’m trying to figure out how far into my relationship with a new boyfriend should I be starting to do sexual stuff and having sex… your thoughts?


Robby’s Thoughts

First of all, thanks for asking for my old man advice, I appreciate that you would think I might know something about this… and of course I feel like I do, but I’ve also never been a young woman, and I’ve never had the worries or fears of experiences the real life dangers of an 18 year old girl… therefore please take any of my advice with a grain of salt. In reality you might also want to ask some older women who have seen some stuff and who have a good head on their shoulders.

Life is WAY easier when we learn from the mistakes of others whenever possible… so definitely seek additional advice from some older, wisers women.

With that said, here’s my thoughts…

This is a choice specific to each of us, there’s no “normal” amount of time required.

The amount of time it takes for YOU to feel comfortable being naked with a dude, without any feelings of pressure or obligation, is going to be specific to YOU. This is one of those life choices that only feels good when it’s on YOUR own terms.

Because sex is so dangerous, especially for women, it needs to be taken seriously. There are real dangers to consider… dangers like pregnancy, STD’s and of course sexual violence.

I’m going to say this for the benefit of any men who will read this post: women are simply born smaller and more vulnerable to a man’s physical size and aggression and therefore have much more serious reasons to be careful around sexual behaviors. I’ve heard stories from women about when they hit puberty every guy they encountered started to treat them differently, and that it can feel pretty strange and dangerous and creepy… because it IS dangerous and creepy!

This is why it’s so important for girls to filter our guys who are overly aggressive, who don’t understand the word “no” very well, or who are not good at caring for a woman’s vulnerabilities. If your boy thinks it’s okay to pressure you then it’s going to be hard to trust he’s doing to slow down when you need him to. I’ve always felt that if a guy is patient and doesn’t pressure his girl to get naked then he’s probably more trustworthy in the bedroom.

I guess that if your boyfriend proves himself to be patient and trustworthy, and shows great care, then the real issue is when YOU’RE emotionally ready to be vulnerable and naked with him.

If you’re mentally ready to handle getting pregnant or an STD… AND you can handle him disappearing the day after having sex with him (this does happen)… and you’re self confident enough to dictate the pace without letting his expectations rush you THEN you’re probably ready to have sexy times!

If you’re not mentally or emotionally ready to handle disappointment or sexual embarrassment, then don’t do it. You’re not ready.

At my age I have seen it all and I can handle it all. I’m obviously very careful with whom I get naked with… because I clearly don’t want an STD, and I also consider my naked time valuable and only the most worthy of women deserve it. And just as I have to earn my way into a woman’s inner juicy vulnerable true self, so does she with me.

With all of those things considered… If I’ve just started dating someone I will definitely have tried kissing her by the third date, even though I want to kiss her on the first. And we will most likely start some petting zoo make outs within 5 dates. And most likely we’re having sex within 8 dates. That’s been my experience, but that’s also my comfort level, and every woman is different.

It’s YOUR job to learn YOUR comfort zone, and be okay giving him those boundaries. Be clear and specific as a way of practicing your assertive self, and as way of keeping yourself safe.

Find your OWN pace and you’ll keep yourself safe and happy no matter the outcome of the relationship.

~ Robby

2 thoughts on “Question: How Far Into A New Relationship Should I Start Having Sex?

  1. Mrkoolio says:

    A man has got to know his limitations. Clint Eastwood.

    Robby….i truly think you are speaking to the wrong audience, your answer was perfect. Perfect….if written by a woman or a sensitive man talking to a young girl.

    You say that when a girl hits puberty, all males treat her differently, which you find "strange and creepy and dangerous". Ummm, it is biology. How she feels is one thing, but for you to conclude as you do, reveals that you look st things from a woman's point of view, much more often than you do from a mans point of view.

    So when a 16 year old boy starts acting differently around a 16-year-old girl entering puberty, can you find it strange and creepy and dangerous. I have never even heard a man express anything close to this opinion. Further you failed to mention that the girls also start treating the boys differently and dressing differently , eyc. Both sides are coming into their oung sexuality. How that is strange and creepy and dangerous is not clear to me. Most of us or thinking about how dangerous sexes, we are thinking about how we can get it 24 hours a day seven days a week . Most young men would happily sleep witn almost any girl, especially to pop his cherry. I dont think most of us view it as something we only share with "worthy women." You know who does that…..? Women. They are taught that ther little v is this special prize hat only a worthy boy should get. Boys are not taught, and they wouldn't believe it or follow it anyway, that their little P between their legs is this special object that should only be shared with a worthy woman.

    And they wouldn't believe it or follow it anyway, that their little P between their legs is this special object that should only be shared with a worthy woman.

    Robert …..either your opinions have been heavily influenced because you grew up being raised by a single mom or there something else going on here. Either way, there is certainly nothing wrong with whatever your feelings are or how you feel about life. You are certainly entitled to your opinion's and you seem to have given great thought to how you want to live your life and all of that is great. I honestly mean that. I am a live and let live person and while i am a true hardass on most things….how people act, or what they believe, or who they sleep with….it is their business.

    It's just that you're holding yourself out as this advisor to young men and 90% of young men from 18-25 are looking for sex first…and a relationship second, if at all. Your advice seems more applicable to young girls. Maybe run it by others you trust. All the best.

    • Robert Belland says:

      Thanks for the thoughtful response. All I can say is that perhaps I explained myself poorly, or perhaps you misunderstand me.

      I've found that most guys don't appreciate how women feel. I grew up with only women so perhaps I have a point of view that's mostly feminine.

      Plus, I'm not sure you recognize that this special article WAS written for a young girl, not a young guy. Hugz?

Leave a Reply to Mrkoolio Cancel reply

Your email address will not be published. Required fields are marked *

Share This