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How can I start casually dating and hooking up with this dealbreaker?

Tagged as: Friends with Benefits, Sex<< Previous question   Next question >>
Question - (11 November 2020) 6 Answers - (Newest, 20 November 2020)
A male United States age 26-29, anonymous writes:

Im a 25 year old male with only 1 sexual partner in the past. How can I start casually dating and hooking up? Im not looking for a serious relationship as i just got out a 9 year relationship 4 months ago. How can i break it to a lady that i dont mind hooking up or friends with benefits, without offending her or coming off as a dick?

Another thing is my past relationship really shook my confidence. I am small in terms of penis size (4 in., im not sure about girth) and i also suffer from Premature Ejaculation. I thought i was able to work it out with my ex, but it seems that when she found someone better she left with a quickness. I dont have a problem talking to women, but in the past i have been rejected right after they saw my penis size. I been embarrassed a couple of times, but i try to stay optimistic. Am i stuck just having to try and find the "right" one that will accept me for me and give up on casually hooking up?

View related questions: confidence, ejaculation, friend with benefits, my ex, my penis, penis size

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A reader, anonymous, writes (20 November 2020):

You are not comfortable enough with yourself or others to be able to get casual hook ups. The sort of guy who is successful with that is far more confident, assured and knowledgeable about life and people, has far more charm, far more oomph. Some women are more promiscuous now but many women are only interested in real relationships and won't be interested in casual. Some of those that are interested in it will be getting loads of offers from men who are good looking and confident, they will not need to go for the others, they would rather not bother then.

If you want more sexual experience and practice then pay women who sell sex, they will pretend to overlook your awkwardness, shyness, lack of confidence and talk to you as if you are wonderful and making them happy too - even when they find you incredibly tedious and boring.

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A male reader, anonymous, writes (18 November 2020):

"rejected right after they saw my penis size."

"They" meaning more than one. So you were at the point of intimate contact and they rejected you because of your small penis? If that's true, that's a real longshot. It won't happen again. as for Premature Ejaculation, try wearing a shirt, maybe she should too. Too much nakedness can be overload.

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A female reader, Dionee' South Africa +, writes (18 November 2020):

Dionee' agony auntYour break up is still very fresh. 4 months isn't a long time at all. I think that you're jumping the gun. Spending 9 years of your life with someone is a big deal and it can hurt very much when it ends. You haven't had time to process everything. Just because your ex has moved on doesn't mean that you have to force yourself to. The healthiest thing to do would be to take some time out and deal with the pain associated with the break up so that you can heal. I suggest that you stay single for a bit and work through all of your emotions and feelings of inadequacy along with your insecurities. It isn't going to help you in the long run to try to cover up those feelings. It's better to deal with them now than to wake up 20 years from now with the realisation that you're still not over it.

I'm not doing to encourage promiscuity but I will say that when you're ready and when it's right, all of the things that you're insecure about won't matter, to the right girl. In order for you to move on and find true happiness, you need to make sure that you're the best possible version of yourself. Until then, take it easy and learn to love yourself first.

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A male reader, CMMP United States +, writes (12 November 2020):

Penis size is a personal preference just like many others things are. Hair color, breast size, nice feet, height, personality type, body shape, etc. You have been rejected plenty of times for other things you just didn't know it or care, but for some magical reason penis size is a particularly sensitive one.

Just look at it as another one of those personal preference things and find the right girl.

Regarding hooking up: if you have chemistry with someone then you can attempt a move. If it doesn't work, accept it, if it does great. Don't overthink it.

Online dating is good because you can be upfront about not wanting a serious relationship.

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A female reader, Honeypie United States + , writes (12 November 2020):

Honeypie agony auntWhy do you HAVE to have casual hook ups?

I mean WHY not process then end of your relationship, take the time to heal and THEN move on?

I know it's a "generational" thing this hook up culture but I think it's so unhealthy for both guys and girls. You think by having many sexual partner you will become a better lover, you won't necessarily be. You will have a higher likelihood of getting an STD (such as HPV or herpes that you HAVE to live with the rest of your life) You think by having casual sex you won't get hurt if they just have sex with you once and move on, that isn't necessarily true either.

To me, casual sex and hook up culture/FWB is a sign that you think sex and people are disposable. You just "use" someone and toss them.

I have seen more times, than I care to remember, here on DC women (especially) getting attached to their "FWB" and getting really hurt when it goes no where, to feel really "used", even though they "signed" up for that.

People are not tissues that you USE and then toss.

Having casual sex with random strangers will not HELP you move on. Nor is it their "job" to do so.

Have some more respect for yourself. Take the time to get over a break up and TAKE to time to find a new partner.

Your penis size has nothing to do with how you should proceed in life. Having standards, being a quality person with values, morals and a personality is more likely to "catch" you a great partner.

Take the TIME getting to know someone. So they don't USE you and judge you for ONE thing only, your penis size.

And sexually there are a LOT a guy can offer REGARDLESS of his penis size. It is not a magic want that makes sex great or not. The person ATTATCHED to it, is the one with the skills.

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A male reader, anonymous, writes (12 November 2020):

Well, in this age of digital communication dating and finding a partner has become so much easier that you can discuss almost anything with a prospective partner before meeting them. I say you should tell a date candidate of your shortcomming in advance maybe you will discover that some women are not particularly hung up on size.

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