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Should I 'go there' with this older friend?

Tagged as: Age differences, Friends, Friends with Benefits<< Previous question   Next question >>
Question - (11 March 2014) 4 Answers - (Newest, 12 March 2014)
A female Canada age 36-40, anonymous writes:

Basically I need some advice as to whether or not I should ‘go there’ with a friend.

So, I have known this guy since I was 20, I am now 24 and he is 40.

We met through work and were good friends.

After I left my job, we did not speak for a while, and then he contacted me again. We made small talk, he asked how I was etc then he told me that he and his partner had decided to separate (he had a gf for over 10years). He told me he had not been happy in a while, and was at peace with it, and that was it.

Since then his behaviour towards me has become a lot more flirtatious than what was, and I now find myself reciprocating to his advances.

About a year and a half after they broke up, we would go out as normal, and then bit by bit we became closer. One night we were out for the evening and ended up making out for the first time. I know he wants to sleep with me (there is a strong part of me that wants to sleep with him too), but the only thing that concerns me is where we will stand after, and how his behaviour changes towards me.

So sometimes, when he is really turned on, he will talk dirty and be quite touchy and indicate that we should sleep together. Other times he is sincere, such as he will say things like ‘don’t doubt yourself, you are an intelligent and kind person’, then he can be normal and jokey, and then the be all moody.

I find it hard to understand what he really wants, I honestly don’t care about our age difference, but I do think there is a part of him that cares about it. Also why does he want me sexually one minute, the back off the next.

thanks guys

View related questions: broke up, flirt

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A female reader, anonymous, writes (12 March 2014):

thanks for the advice all.

yes, there is apart of me that thinks he is testing the water for sure. Maybe because it has been a while since his last relationship and he was in it for 10 years, this whole fwb/ fooling around is new to him and hes not so good at it.

I'll see where it goes, i don't want anything serious i just dont want to be messed around/ strung along if you get me because we are still friends and i dont want to lose that.

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A female reader, Honeypie United States +, writes (12 March 2014):

Honeypie agony auntMy advice, don't play with fire if you don't want to get burned.

The reason he is going back and forth is because he is testing his boundaries and maybe he is a bit unsure about taking it further.

The thing is, he might not mind a young girl in his bed, but since he had made no attempts to talk about DATING you, my guess is he is holding back because he is worried that YOU might want more then just flirty banter and a few rolls in the hay. And it can also be that he feels like IF he took it further it would be like taking ADVANTAGE of you.

He isn't looking for GF. If he was he would treat you VERY differently.

So my thing is,what do YOU want? A FWB? or a friendship?

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A female reader, Alba5 United Kingdom +, writes (12 March 2014):

I don't think the age gap is a problem there were 18 years difference with my granparents and they had a very loving and happy marriage with each other. I think he respects you thats why he is a bit hot and cold with you, and maybe doesn't want you to think he's taking advantage of you. It's been over a year that his relationship has finished so it's not as if you are a rebound thing.

I'd say if you really want to sleep with him then do it. You obviously like the guy.

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A male reader, Danielepew Mexico +, writes (12 March 2014):

Danielepew agony auntI think a 24 year old shouldn't be with a 40 year old. Sorry.

Yes, there is a part of him that cares about being 16 years older than you are.

But if you think age doesn't matter, then, before you do anything, find out where you would stand if you slept with him. Find out for sure.

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