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Casual relationship with friend/roommate has become more for me but I don't know how to tell her

Tagged as: Friends, Sex<< Previous question   Next question >>
Question - (26 May 2012) 5 Answers - (Newest, 28 May 2012)
A male United States age 36-40, anonymous writes:

I'm in a situation that I am very confused and emotionally frustrated about. At the beginning of the year I moved in to an apartment with one of my best friends (who is female). For awhile things were going as a normal roommate situation would... Then, on occasion, she would wind up sleeping in my bed. It was strictly platonic to begin with. After a month or so it became a regular thing for her to sleep in my bed. Pretty much every night she was there. Then we started cuddling before we slept and while we slept. Well that lasted about another month. Then one of my good friends gets a job in the area and needs a place to live. My roommate suggests that he takes my room and I go into her room. This was HER idea. So we do that and after a week of that we started having sex. We have only done it twice so far.

Here is the issue. She has always been a good friend, a great friend but I am madly attracted to her both emotionally and physically. She knows it too just not to such a high degree. I feel like she shares some feelings towards me but I am afraid to ask cause I really don't want this to be awkward. She says many times tha she wants to be single and do what she wants. However, she told me she got angry at me one day when she read some casual conversation I was having via text with another girl. I think she may have gotten jealous. Is this a situation that I have no hope of getting a good ending from. What does it all mean? It clusters. It when I see her flirt with guys and such. I'm the last guy she has slept with. I keep hoping that she just doesn't want to be exclusive yet for whatever reason... What do I do?

View related questions: best friend, flirt, jealous, moved in, roommate, text

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A reader, anonymous, writes (28 May 2012):

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

She knows how I feel. She knows that i would be all over any opportunity to be her boyfriend should it present itself. We have not had sex since last Sunday. But evey night we are cuddling and sharing our bed. I feel as though she may be keeping her options open? Or she wants more attention in being single? Or perhaps she doesn't even realize she has feelings in return? This situation is way more complex in my eyes than I can possibly explain. Could a girl really volunteer to have her guy roommate move into her room so someone else can take his room and not have any feelings at all? Ahhhh

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A male reader, The Realist Canada +, writes (26 May 2012):

The Realist agony auntHere's what I would do; plan out a date for the two of you (something romantic) and see how she reacts to that. Once you explain that you would like to take her to dinner and such she will realize that you are asking her out on a date. Then that opens up another opertunity to have that conversation again.

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A female reader, The Girl with the Diver's Hair United Kingdom +, writes (26 May 2012):

Seriously, TELL HER! She's playing hard to get when she knows for a fact that she feels the same as you do. I reckon she's just waiting for you to make your move! So go for it! Good Luck.

E x

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A female reader, anonymous, writes (26 May 2012):

She is openly showing that she is interested, you sleep together and you are afraid to tell her you like her and want to be more than friends?? Tell her now. what is the worst case scenario? She may say no I want to be FWB so you already are. You won’t lose anything. The only problem is if you continue like that she may lose interest as she realizes that you do not want more from this relationship or she may find someone else. Hurry up then

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A female reader, YouWish United States +, writes (26 May 2012):

YouWish agony auntBoy, you missed a golden opportunity in the conversation you had with her when she stated that your communication with another girl got her jealous. That was a wide open invitation to tell her how you feel.

Luckily for you, the door is still open! Just open the conversation with her by referring to what she said..."I've been thinking about how you said you got mad at me for texting another girl. I'm interested in being more than Friends with Benefits. I have feelings for you and want to be more than friends. Truth is, you're the only one I want to text with"

Go slow, but tell her that you want to pursue being more than friends with her, and take it slow. Don't start up the "exclusivity" conversation until you've talked about properly dating her. A FWB situation isn't a relationship, so you have to start from the beginning, and that's to start asking her OUT. Ignore the fact that you've had sex with her and ask her out properly.

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