How to find casual sex opportunities to gain experience and confidence?

I am just recently out of a relationship and marriage that lasted around 13 years. I am in my late thirties.

I met someone recently via an app, and we have been having sex (though I have experienced a lot of performance anxiety, and thus have had to rely on Viagra, unfortunately).

Part of me would like this connection to develop into a relationship, but another part of me recognises that this may not happen and is interested in doing things that I simply wasn’t capable of (owing to erection problems and a profound lack of confidence) when I was younger. Because of my historic problems with erections, I have hardly had any partners (i.e., for full penetrative sex), and now that I am no longer married, I perhaps would like the chance to explore. Sex for me has always taken place in the context of a relationship.

The thing is, dumb as it may sound, I don’t really understand how to access opportunities for one-night stands and casual sex. When I read online, everyone seems to have had these opportunities (some enjoyable, some not so much).

I am an in-shape, fairly attractive guy who can hold a conversation. I have been on dating apps and have been out with a few women over the past few months, only one of whom I decided that I wanted to sleep with. I find dating apps hard work because it’s rare to get attention from a woman that I feel I’d like to have sex with, and most of the women do not seem to be interested in casual experiences in any case. People always refer to Tinder as a hook-up app, but I haven’t got a clue how to use it in this way.

I’ve never had one-night stands or sex outside of a relationship, and it kind of baffles me how it’s done. But lots of people seem to hook up all the time.

Does anybody have any tips please?

Have you tried Tinder/Bumble/Hinge (if straight) or Grindr/Scruff (if gay)? How about DoubleList (the log-in Craigslist…)? There also is the bar or asking someone out at places you go (or don’t go).

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Thank you - I have tried the apps, with only moderate success. I’m in my late thirties and it’s a bit of a struggle to find anything casual, so maybe my age is counting against me.

With apologies for the dumb question, is it basically a case of treating this as a numbers game and being willing to keep putting yourself out there?

I am a pretty good-looking guy (not a head-turner, just attractive enough), in shape, educated and can hold a conversation, so I wouldn’t say that there anything’s especially against me. I probably need more “game” though!

Hi there, couple things:

  • why do you need to have casual sex?
  • have you tried therapy?
  • is you ED psychological? If yes, I don’t think it is a good idea to use Viagra
  • what you current goal - have more casual sex or overcome your ED?


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Thank you for your reply. It’s a bit of complicated answer.

I have had therapy a few times in my life, yes. Unfortunately, at the moment, it feels like a matter of either using Viagra or not having penetrative sex.

My current goal is to overcome my ED, but it is proving challenging to do this with the person that I’m currently with (as much as she has been very understanding). I get the impression that people in wider society have had a lot more casual encounters than me, and I feel that I have missed out and am a lesser person as a result.

The woman that I’ve been seeing - who is wonderful - had a string over one-night stands when in her early twenties many years ago. I did not open up the conversation about how many men she had previously slept with; it came up in conversation because she notified me about a permanent STI (which apparently would have resulted from one of three one-night stands). There were apparently many other one-night stands.

She said that “[The number of men] is a normal amount… It’s under 20.” Unfortunately, while I recognise that this is not huge, for me, this isn’t a normal amount - it appears to be really quite high (based on research online), especially at what would have been a relatively young age. It is “normal” if you say “It’s having sex with two different men a year, for a few years from school, through university and while travelling after university…”, but it still feels like a lot. A few one-night stands would be fine with me - all part of life. But I wonder why there were so many and she wasn’t inclined to enter into relationships. She says that she’s not ashamed of her past (and I’m not trying to make her so), but it still eats away at me.

I was previously married for years (and in relationships prior to that), and she is only the fourth women that I have had penetrative sex with. I likely would have had penetrative sex with more women had I not been scared of sex (I lost my virginity at the age of 22) because on a set of failed attempts at 17, but it is what it is.

I have really struggled with this on an emotional level, rather than a rational one. But there is a such a huge disparity in our respective numbers, and subconsciously I don’t see how I can possibly measure up and why she would repeatedly jump into bed with men after a single date (I know, women enjoy sex too… It was a long time ago… Not everyone is looking for a relationship…). We slept together on the fifth date, and it had been a romantic experience in the run-up.

Are there advantages to being with a woman who’s slept with a fair few men? Sure thing, for a secure guy (who doesn’t have ED).

But I find her past intimidating and oddly disturbing, and it suggests to me that I have values around sex that conflict deeply with hers. Is it sensible to enter into a committed relationship with someone if I feel this way? I am really trying to let the emotions and thoughts pass.

But maybe I need to challenge these values as part of getting over my ED, and casual sex (obviously, after ending things delicately with her) feels like a route to do this. Maybe penetrative sex isn’t such a big deal? If I have more experiences with women, then wouldn’t it be easier to accept the (almost inevitably higher) numbers of any woman that I would like to get serious with in future?

I appreciate that this may not sound rational, but it’s where I’m at.

I think the apps have been out long enough that people are bored with them or do not find them sexy anymore. Initially fresh cookies out of the oven were exciting. But they are made everyday and less something people seem to go out of their way for now.

I’m same age as you and also find it more difficult to use the apps now, but also am more picky. I could lie about my age or go to a different city for a weekend as I see other guys my age doing. But that’s a lot of work to go to a different city and against my values to lie about my age since it just contributes to the online dating lie even more and seems to reinforce lack of trust of age of older people by younger.

People do turn heads at me in public, but I always assumed I just have good posture and am fit and shy away from the attention.

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I’m asking about therapy as I believe that it could be very helpful given your current situation. Forums and apps are fine, but talking to a real person could be really beneficial.

You often use the term ‘penetrative sex’ and refer to partners as ‘numbers’. Why is that? Do you think that ‘no penetration’ equals ‘no sex’? And why do you compare your sex life to those of other people?

Based on what you wrote, it seems that you often compare yourself to others. At the same time, you often judge others and yourself. Although it is normal, it might become unhealthy in the long term. I would try to find the underlying cause for such behavior.

It is normal to want causal sex. It brings you excitement and novelty, something you don’t always have when in a serious relationship. At the same time, it stresses you out because of your past experiences. I would personally look for excitement and joy elsewhere. Try out new things like courses, sports and hobbies; travel more, go hiking, try meeting new people everywhere you go etc. This will help you to feel better about yourself and to eventually meet potential partners (casual or not).


Thank you for your thoughts - much appreciated. I hear you - I will consider some therapy options.

I am referring to partners as numbers because I am insecure about the substantial disparity in past sexual partners between my new partner and me. As I mentioned, I feel that my sense of confidence would increase if I were to have experiences with other women. On an emotional level, this is the result of an acute sense of low self-esteem and shame that I was not able to have more experiences, envy at hers (young women do not seem to have to “work” for sex to anywhere near the same degree that young men do), and a degree of disgust at her number and the fact that so many were one-night stands (I am not giving her a hard time about my feelings, which I am responsible for - I am just being honest here about my problem, which is in my head).

Ideally, my marriage would have worked out and none of these thoughts would cross my mind (I never worried about “numbers” in the past), but that’s life and I can only look forwards.

I completely recognise that “penetrative sex” does not equal no sex. I have given my current partner multiple orgasms using my hand and mouth. But penetrative sex is what I struggle with, erections-wise, and thus it takes centre-stage in my consciousness. I have worked to compensate for my inadequacies over the years by being a careful, attentive lover who is much more than a (unreliable) penis.

Thank you for your insight re comparisons and judgement. This is definitely something for me to explore and address.

Part of wanting casual sex is about self-development, exploration and growing as a person, not only in relation to confidence in my erections. I am typically the guy that women seem to want as a long-term option; I am supportive, stable and nice, but I’m not an exciting casual sex option. Could I develop this version of myself too? Is it possible for me to be this guy too?

I don’t think casual sex does stress me out, in fact. I find sex tougher when I care about the woman that I’m with. All my focus is on making her comfortable and not feeling like a brute. What I don’t understand, as I mentioned at the very outset, is how to seek out and secure opportunities for casual sex; it’s not the act of casual sex that is stressful per se.

Your point about seeking joy elsewhere in life is great - thank you. I am involved in a fair few things outside of work, and I will make sure that I focus on other avenues to explore life and take the focus off sex.