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How do I ask him if we're going to get together?

Tagged as: Friends, Troubled relationships<< Previous question   Next question >>
Question - (13 June 2012) 2 Answers - (Newest, 15 June 2012)
A female United States age 30-35, anonymous writes:

dear cupid,

soo, there's this guy...who we'll just call ryan. he and i met back in january and started "talking." we both thought that we were going to wind up actually dating, but life kind of got in the way, and a relationship between the two of us apparently just wasn't in the cards; when it all came down to it, we were dealing with love from the past that we just weren't ready to part with...not even to take a chance at what we both knew could have been a really beautiful thing between the two of us.

even though we opted out of taking a shot at romance with one another, ryan and i remained really close friends and talked all the time. our quests to restore those past loves that we were both still clinging to were most definitely not easy; there were a lot of hardships, and we both ended up getting our hearts broken repeatedly. we were there for each other through all of that, and in a way, i feel like it's brought us even closer together.

eventually, we began engaging in sexual intercourse and things of that sort with one another and even started to talk about the possibility of really giving romance a serious try this time. the thing about us is that we're both just incredibly stubborn little fighters who don't really know when to walk away. we broke each other's hearts and kept pressing toward the goal of regaining the love that we had lost with other people. this caused a few squabbles between us because of the timing in which things took place--whenever i was totally sure that i wanted to be with him, he wasn't really sure if he wanted to be with me, and vice versa. but when it all came down to it, neither one of us could stay mad at the other for veryy long at all, and like everything else, i feel like those squabbles have brought us closer together.

we've finally given up on those lost loves, but ryan and i are still not getting anything going between the two of us. right now, i guess the best term for us is "friends with benefits," as we still engage in sexual activity on quite a regular basis. we also talk literally every single day, even if it's only a text saying "hi." we hang out just about every chance we get; sometimes, we don't have sex--we just hang out and talk and act stupid together like close friends do. there are even times when we don't even do any of that stuff; we're basically just doing our own thing and happen to be in the same room as one another. and no matter what we're doing, it always feels entirely comfortable--like, there's no pressure, and it's never awkward or anything like that.

like i said, right now, ryan and i are pretty much just friends with benefits. however, i'm starting to get back into that phase where i want us to be more than that...and he kind of makes me think that he feels the same way.

for example, i recently went on a trip to galveston with the ex-boyfriend that i've been trying to work things out with; it was kind of a last-ditch effort to save us. i was hanging out with ryan the night before, and we got to talking about the trip. ryan had known ahead of time that i was leaving...he just didn't know who i was leaving with. i decided to tell him (it just felt like something i should do), and we ended up getting in a squabble over that.

we forgave each other pretty much immediately, though, and he texted me quite a few times while i was away to ask me how things were going. when i arrived home, i told him the whole story about how things hadn't gone as well as i had hoped that they would, and although he said he was sorry to hear that, his reply was something along the lines of, "i got really worried because i didn't want you and him to get together, i wanted to start hanging out more."

i ended up going to hang out with him that night, and things were pretty much the same as they always were whenever we hung out--we joked around, we flirted, we got intimate...and this time, we even ended up having a conversation about all of the things that we like about one another.

i plan to see ryan again really soon, and when i do, i would like to find out where we stand...as well as whether or not he's been behaving the same way with anybody else. the thing is, i don't really know a good way to go about doing that. like, i feel like i can talk to him about anything...but for some reason, the thought of just asking him straight up, "hey, are we gonna get together, and are you having sex with anybody else?" just makes me really nervous and seems a little weird to me.

based on this information, what are your thoughts about ryan's feelings for me? and how should i go about finding out the things that i want to know?

View related questions: flirt, friend with benefits, text

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A female reader, Dorothy Dix Australia +, writes (15 June 2012):

Hi there. It seems that you have a pretty good rapport between you, but there is still some emotional baggage you are both carrying around from your previous lost loves.

There is no doubt whatsoever that this is getting in the way of you and him getting together as a couple.

It's also possible that you are both putting too much emphasis on becoming a typical boyfriend and girlfriend status, and this becomes an issue when you are both reminded of past failed relationships.

So the real problem here, is that you both need to learn to trust people again, and to realize that not every relationship is going to fail.

History isn't going to repeat itself, while ever you only live in the present moment.

And the present is all that we have.

Why not take all the focus off whether it could work or not, and instead just concentrate on enjoying each other's company and having fun together.

Then you are not going to remind yourself of what happened in the past.

If you genuinely like each other, well then there is no reason why it can't flourish between you and him.

Just take being a couple right out of the equation for now, and see how things go just being friends - as you are now.

Then over time and without pressure for there to be more, it will probably just naturally evolve into a boyfriend and girlfriend status, which is what you both want.

In the meantime, you both need to let go of the expectation that there should be more between you.

It serves no real purpose.

And just let things happen on their own, the way there were always meant to.

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A female reader, anonymous, writes (14 June 2012):

Well you already told him you like him a lot. Tell him the rest and see what he says. That way you are not asking questions and hopefully he will open up. One way or another you should find out whether you are more to him than just friends with benefits. It sounds to me like you are, but I haven't heard his side so GO FOR IT!

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