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Should I be open to casual sex to gain experience?

Tagged as: Big Questions, Sex<< Previous question   Next question >>
Question - (17 January 2018) 14 Answers - (Newest, 21 January 2018)
A male United States age 26-29, anonymous writes:

I am a 25 yr old male with a problem in dating/sex I cant figure out.

I am finishing medical school this year. I put in a lot of work/long hours to get where I am. I go to the gym try new hobbies etc.

I was shy in high school,got better in college but not where I want to be. Ive had some bad rejections by women along the way. Had a girlfriend in high school too soon to have sex with.

Ive only had sex with one girl a few times. I dont feel confident sexually. I have had foreplay with a handful of girls where I always put the girl first since its such a rare opportunity for me so I get good feedback.

The few times I meet a girl that likes me she always wants something very long term and I dont have the dating experience/don't want to lie to them to want to settle down now.

I missed out on a college experience and have this thought that I need to have casual sex to practice for a girl I really like. Plus it would make me very insecure since most girls already my age have plenty of experience with sex.

That makes it even more intimidating to approach them. Im kind of kicking myself because my friends have a good amount of casual sex and I feel less masculine than them.

I guess Im asking if its ok to go out now and try to have casual sex to gain confidence and if its understandable what Im feeling in my position?

I dont want the next girl I meet to be the one I end up with since I have little ability to compare what I like in women both in a relationship and in sex.

Also there is some self loathing with the lack of sexual partners that would make a relationship with a girl with a lot more experience tougher.

View related questions: confidence, foreplay, gain confidence, insecure, shy

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A female reader, Andie's Thoughts United Kingdom + , writes (21 January 2018):

Andie's Thoughts agony auntEven your therapist told you it's about your confidence and anxiety, not sexual inexperience. Just focus on going out, having a good (SAFE) time and perhaps a few casual DATES, not hookups.

Try to be less picky because apps match you for a reason. If you make sure they're only interested in casual dating, you should still consider going on a couple with girls you'd otherwise rule out. Most of us wouldn't have met lovely people if we'd jumped the gun and dismissed them before meeting once or twice.

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A male reader, anonymous, writes (21 January 2018):

Hi again, OP here.

Just want to assure male anon that I have taken rejections before and while some hit me harder than others Ive been ok otherwise. My current outlook is kind of pessimistic like "oh if this girl rejects me its ok since it would be nothing new".

I saw a therapist about a year ago and his conclusion was just a lack of confidence/bad luck on my part because he didnt find anything wrong with me/noted my anxiety due to inexperience, and said I undervalue myself.

Update:I went out to the bar scene near my apartment and its good for dancing/people my age. Might try it repeatedly. I have a few dating apps but never really match with many people I like. My pictures are quite old though

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A male reader, anonymous, writes (20 January 2018):

Hi, something about your original post worries me. I think it probably would help you to talk to a therapist. You sound so anxious that I think the inevitable occasional rejection would be quite painful in your current state.

What you should be after at the moment with women is not just an investment in the future, but good, fun experiences.

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A female reader, Andie's Thoughts United Kingdom + , writes (20 January 2018):

Andie's Thoughts agony auntSpeed dating. New hobbies. Ask female friends about dating.

OP, please don't think women "don't like fumblers". With all due respect, it's rubbish. Sure, some women are impatient, but most just want a decent guy who makes them happy and wants to LEARN what they like. No woman likes the exact same thing, so having multiple casual sex experiences will NOT help you with women - the same way that porn doesn't give you a realistic view of sex.

If you want casual sex, go for it, but do NOT be "delusional" in regards to why. It will NOT give you confidence or useable experience. It will give you meaningless, emotionless sex and possibly a negative reputation. If you just want sex, do it, but it won't help you with real life women who want a relationship with you.

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A male reader, anonymous, writes (19 January 2018):

You have a very antiquated idea that getting experience in sex equals sleeping around casually.

I won't reiterate what others have said, but I'll add that a lot about being good at sex is not being selfish. You seem to have get it a little, but not enough. For women, sex is very mental. There has to be a situation and a mood setup.

In any case, I doubt you'll ever get there thinking like you do. You need to get over this limiting belief that more experience equals self worth. With more experience you'll become more jaded and end up not enjoying anything you're doing with a lady in the first place.

Enjoy the journey, stop thinking too much and trying so hard. I recommend meditation and relaxation when you have ruminating or self defeating thoughts.

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A male reader, anonymous, writes (18 January 2018):

Hi, OP here.

Good advice here I appreciate it.

Just to clarify, I do have several female friends I am close with. I am not exactly sure what you guys mean by interpersonal relationship experience I am missing because I have several female friends I talk to, who I know think highly of me and it is platonic. Even they wonder why I am still single but they know its due to lack of confidence(we talk about pretty deep things).

I dont think its helped me be closer to a satisfying dating/sex life by having female friends. Maybe just the edge off of talking to women.

Talking to women I dont know, forming a connection, showing interest, dating leading to sex seems so daunting when I am anxious others have more experience with it, women won't appreciate a fumbler, being a disappointment etc.

Its hard to meet people after college too so I thought going to bars and at least socializing with people I dont know might help me loosen up.

Ive got some free time now that school is winding down these 6 months

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A male reader, N91 United Kingdom + , writes (18 January 2018):

N91 agony auntI know a few people who have slept with 100+ females but there's rumours that go around that they're terrible lovers. Having sex with more people won't magically make you better in the sack.

You do whatever you want, if you want casual sex go and do it. But I don't think you'll gain much from it. I'm 26 years old I've been there and done the whole trying to sleep with as many women as possible thing. You don't get a medal or a pat on the back, you get nothing, because it's pointless. You don't gain confidence by sleeping with people you couldn't give a fuck about. You gain confidence by forming deep connections with people. It doesn't matter if you've slept with 1 person or 101 people, you become a better lover by experimenting with different things and seeing how the person reacts to what you're doing. You will become a much better lover by communicating with someone and asking what they like rather than trying to sleep with a whole bunch of people you're never going to contact from the morning after.

You'll learn a lot more from trying to be social with people, talking and conversing. If you doubt your sexual ability then that's something you can work on with someone that means something to you.

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A female reader, Andie's Thoughts United Kingdom + , writes (18 January 2018):

Andie's Thoughts agony aunt"wiseoldman" I'm sorry that was your experience, but most women don't care if someone fumbles and is inexperienced. In fact, more women prefer someone who was patient, instead of someone who had lots of casual sex.

All casual sex will give you is a temporary high. The long term effects are low confidence, as you're still no further ahead with women, and a potentially dodgy reputation among women.

If you want casual sex, go for it, but you won't gain anything useful. It won't make you better with women because everyone is different and you'll need to learn their likes and dislikes, not something casual sex will teach you.

Most women your age do NOT have loads of sexual experience because the majority prefer to be in relationships, not sleeping around. Some do, but then they're not necessarily right for you.

Something we often see with men in your situation is that you're going for women "out of your league" or just not being realistic. One of the main issues you will have is that most women your age DO want a relationship, not just something casual.

The second huge issue is your lack of confidence. Women don't like cocky men, but men who frequently put themselves down aren't approachable.

Most women don't want guys who have been around a lot. Some accept it as their partner's past, but most would rather it was lower. All you do is share fluids and meaningless experiences with random people - not something that is appealing when looking for a partner.

Honestly, it would be silly to dismiss the advice, as the majority are telling you it's foolish to expect casual sex to make you feel better. In order for anything to improve, you need to work on your basic experiences with women, not your sexual experiences. Do some speed dating and online dating - just make it clear you're only looking for casual dates (NOT casual sex!), for now.

For what it's worth, focusing on the woman's pleasure is EXACTLY what most women want/need, as too many men don't - particularly guys who have had several hook-ups. If you keep making sure they're satisfied, they are likely to find your lack of experience irrelevant, if not a bonus!

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A female reader, Honeypie United States + , writes (18 January 2018):

Honeypie agony auntI don't think you will gain MORE confidence by having more casual sex.

More partners does NOT equate to becoming a better lover. Why? Because each person is different. Likes different things (in and out of bed). It's not like the medical text books - body part a goes into body part B...

I agree with FA, you need more SOCIAL experience. Interpersonal relationships.

And I fully agree with YCBS, that casual flings will probably NOT help you gain confidence at all. Because casual "Tindr hook ups and the likes) is all about one thing - instant gratification. NOT good sex, not LEARNING new things and getting good at them, not about being a decent guy. It's not about getting to know YOU. It's TRANSACTIONAL sex. You might get to climax, she might get to climax then off you go to someone else... I mean really? How is that going to make your more confident? Because you stuck your penis into multiple women?

I think you need to rethink that attitude.

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A male reader, Garbo United States +, writes (17 January 2018):

Garbo agony auntYou being educated, you’d appreciate this significant statistic which says that the more partners people have been with, less happy they are with whomever they end up with. The converse is that less people you’ve been with, happier will you be with whom you end up. You can look this statistic up, even thou, for all its significance, it is being “buried” by the sensationalist media.

Having this in mind, I’d suggest, like other have mentioned, to look for a serious relationship, to find a woman that you really like and one that likes you back. You will gain a great deal of sexual experience with her and it will probably be much more rewarding that random encounters.

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A male reader, wiseoldman United Kingdom +, writes (17 January 2018):

At the risk of garnering the hatred of all too many of the 'aunties' here, gain experience in any way you can. You're still a young man, and I learned the inexperience I unfortunately displayed in my own younger days taught me that women hate fumblers.

Continuing to pour oil on troubled fire, I aver that one CAN learn something from every encounter if you approach your intrigues decently/ethically, and yes, that can be done.

Experience does breed confidence, with the proviso that while rejection will not hurt as badly, success will never feel as good. Nevertheless, the facility gained can be regarded as an advantage in pursuing your more 'important' encounters, and every man needs that element in his armoury.

If I've spoken too plainly, ladies, it's only necause I can only relate my own reminiscences as a battered veteran of the erotic wars, and I hope your opinions of me and this post are leavened by the very truthful assurance that I've been married and faithful for over 11 years.

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A female reader, Youcannotbeserious United Kingdom + , writes (17 January 2018):

Youcannotbeserious agony auntYou seem to be under the impression that you can only gain "experience" by having multiple partners. What is wrong with experimenting and gaining experience with ONE partner? There are many people in happy long term relationships who have had little, if any, experience outside that relationship. They have simply grown together and don't feel the need for sex with others.

You do not need to "compare" to know what you like in women. You already KNOW what you like personality wise. As for sex, you learn together and get to know what you like.

Given your insecurity, I doubt casual sex will help you gain in confidence. If anything, it will make you feel worse as, with casual sex, you are judged solely on one, or a handful, of encounters. It is all about "performance" and you do not have the experience yet to give a good "performance".

In your shoes I would concentrate on finding someone I liked as a person, then stepping into this adventure of discovery together.

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A male reader, WiseOwlE United States + , writes (17 January 2018):

You are a well-educated and intelligent man. You're studying to be a doctor!!! A noble and compassionate profession!

Dude, seriously?!!

Anybody can have meaningless sex! That's exactly the problem in our society and what pisses women off about men! You cannot be serious with this post!

You must practice connecting with women on all levels. If you're inexperienced as you say, that is exactly what you should be doing. How do you millennials get these notions in your heads???

Women for the most part do not like being objectified. If you just want to practice having sex, get a blow-up doll. The best women want something more than just lending you their bodies to get-off, and just go about your business. Hit it and quit it!

What's the self-loathing stuff about? I think you should work on self-confidence, liking yourself, and establishing meaningful relationships. Seek connections with females that require you to practice sensitivity, emotional-attachment, impulse-control, verbal-interaction, and communication-skills. These are necessary; so you can connect with women on all levels. Also to connect with patients professionally and objectively; but on a human-level, and not like an android robot.

If you've been diagnosed with Asperger's Syndrome; then I could understand where you might be coming from.

There are women who would love to use you and discard you afterwards. Those are usually one-night stands, hookers, and STD carriers. Operating with an egocentric-mindset and behavior becomes habitual; and predisposes you to become just another narcissistic self-indulgent meat-headed dick who emotionally destroys good women before decent men can find them. You're better than that. Thank God you're still so young!

Reset your though-patterns, my friend. Seek to meet women and enjoy spending time with them. If sex becomes a benefit; then make sure you know what she's thinking before you bed her.

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A male reader, Fatherly Advice United States + , writes (17 January 2018):

Fatherly Advice agony auntYou don't need sex experience, you need relationship experience, and I do suggest casual relationships (non sexual) to build up confidence in this area.

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