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Should I just ask him bluntly if he wants to go further?

Tagged as: Friends, Sex<< Previous question   Next question >>
Question - (5 April 2010) 14 Answers - (Newest, 8 April 2010)
A female United States age 30-35, anonymous writes:

So me and my best friend and I have been messing around, like I've been giving him handjobs and he's been touching me. The first time I saw him after the first time it happened he acted awkward and we didn't do it again, so I texted him and told him that I wanted to keep doing it, so we've done it a few more times and we explored each other a little more last time, and I would like to go further, but I'm not sure if he does. Is it ok to just bluntly ask him if he wants to go further? Or should I just try to? Or should I wait for him to try to go further?

View related questions: best friend, hand-job, text

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A female reader, celtic_tiger United Kingdom +, writes (8 April 2010):

celtic_tiger agony auntWoooah, slow down!

Already, after just a bit of fondling, handjobs and fingering, your brain is already thinking about relationships and getting "official".

He is your best friend. Have you thought that is all he might want to be? Men are funny creatures, if you offered it on a plate to him, he probably wouldn't refuse, but that doesnt mean he wants you as a girlfriend. At the moment, he thinks it is fooling around, and he has already shown he isnt 100% convinced by it, you were the one that pushed the situation, and how many guys would turn it down?

"So I definitely need to not only ask him if he wants to go further sexually, but also further as in be in a relationship"

Handjobs do not equal a romantic relationship. Just because you have sex, does not mean he is your boyfriend. All you are is friends with benefits, whether you like that term or not, he has no obligation to you, and can go and do the same thing to other women as he pleases. Could you cope with that?

I think you need to slow down and back off, if you actually want to take your friendship to a different level and have a romantic relationship with him, then you need to tell him how you feel, but not by having sex with him, doing this will not win him over, he will only see you as a cheap thrill.

You are already in Girlfriend mode (and I know this from personal experience). You want more, you want a "relationship" and for the touching, handjobs and possible sex to lead to something more permanent and more serious.

"just hoping this is the beginning of something more"

You WANT more, but does he? Do you value him as a friend more than a boyfriend? If he said no, could you still be his friend? You need to figure out what is really important. Then you need to sit down, face to face and tell him how you feel.

If you rush this, have sex with him, and then he tells you NO to your face, you are going to get very very hurt, and you will lose not only a prospective boyfriend, but also your best friend. Be careful. Sex and friends DO NOT MIX.

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A reader, anonymous, writes (5 April 2010):

This is verified as being by the original poster of the question

Thanks so much for all the advice! I actually thought about the condom thing, ChristineAvril...

justwondering13 - yes, it's kind of like "friends with benefits" I guess, but I don't like that term, and it has never felt like we were just friends. He's moving away soon so I think we are apprehensive about going more official, though I wouldn't mind it. I'm just hoping this is the beginning of something more. So I definitely need to not only ask him if he wants to go further sexually, but also further as in be in a relationship

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A female reader, ChristineAvril United Kingdom +, writes (5 April 2010):

ChristineAvril agony auntSimply say "I've got some condoms in my bag"........

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A male reader, anonymous, writes (5 April 2010):

ask him, communication is very important for something like this if you want both of you to stay comfortable. the worst that could happen is he says no and you stay where you are, but at least you know where you stand

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A female reader, Laura1318 Malaysia +, writes (5 April 2010):

Laura1318 agony auntMake sure that you practice safe sex.

To asked bluntly or to just go ahead?

Some just take it without asking.If he did not resist, that means he silently agrees.

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A reader, anonymous, writes (5 April 2010):

ask... Don't do nothing you might regret or mistaken for as something else it's just your privates get heated don't mean anything... Lol

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A female reader, janniepeg Canada +, writes (5 April 2010):

janniepeg agony auntA best friend is not someone I would mess around with. You are crossing boundaries. You are no longer just friends but not lovers yet, just in an awkward limbo stage where you have to make things clear about where you guys stand. If you are ready to accept a NO then definitely ask him.

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A reader, anonymous, writes (5 April 2010):

I know you didn't ask this, but is this a "friends with benefits" type deal? If so...I'm going to highly suggest not to do this. But I'm not here to preach. So I won't go into further detail. With that said, if you love him and want to be in a relationship with him, then things will likely naturally progress. OK, that's all I'll say on that.

Long story short, if you want to go further with him, simply suggest it. There shouldn't be any harm/shame in asking. He'll either say yes or no, then you can take it from there. He may not be comfortable taking the first step and may be concerned that it'll hurt you or something.

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A female reader, calilover22 United States +, writes (5 April 2010):

You need to communicate so yes I think you should ask him. You cant always rely on body language and if he is your bestfriend then you shouldnt be so uncomfortable asking him.

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A female reader, anonymous, writes (5 April 2010):

Nature will show you the way. Follow your instincts, be safe!!

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A female reader, nikkiii23 United States +, writes (5 April 2010):

I think you should ask him to see how he feels about the situation. You don't want to just go further if he doesn't want to, and you don't want to just be used as a sex toy if that's all he wants from you.

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A female reader, anonymous, writes (5 April 2010):

If its your type of personality that you ask bluntly I think thats the best. Theres no rules of how to do things, it depends on the person. If he's more like a silent type and go with the flow, just see what happens.

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A female reader, clvx33 United States +, writes (5 April 2010):

clvx33 agony aunthi,

I'm 14 years old and i have been in this situation. except i didn't wanna do it again with my best friend. If you're really close to him and know how he feels about things then that might help you. if he did it again then he obviously does want to but maybe he is scared to ask you. If you wanna go further, the next time you guys fool around just ask him. hope this helps :]

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A male reader, CaringGuy United Kingdom +, writes (5 April 2010):

I think you need to ask him. You don't want to wind up being used.

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