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We're both about to be single -- should I tell him how I feel?

Tagged as: Friends<< Previous question   Next question >>
Question - (21 February 2013) 3 Answers - (Newest, 22 February 2013)
A female United States age 41-50, anonymous writes:

Hi there,

this is driving me nuts, and I'm not sure if I should move forward and do this, so I figured I would ask a forum of people! hope you guys can help me out.

So, about 6 years ago, I met an awesome guy at work, after he was hired to help our team out for a few months. My first impression of him, well, not so good because he was wearing these really bad coke-bottle glasses. Well, after getting to know him, turns out, he's a really good guy.

Year 1: After his 3-month stint with the company, his term is over, and we don't see each other anymore. He calls me every so often, to talk about...nothing. At first I thought, "This guy wants a job again", but then later came to the realization that "maybe he just wants to talk?"

His mom passes away that year, and since I wasn't a good friend at the time, I sent my condolences and leave it at that. We don't talk for 3-4 months while he recoops.

After he invited me, I take a friend with me to one of his live shows (he's a VERY good looking musician) where I meet 2 of his friends. After being somewhat "ignored", my friend and I leave the venue (head facing downwards) after the show is over. I hear him yelling behind me, and see him running towards me to ask me if I want to do anything after the show. Like a girl in high school, I said "cool" but on the inside, my heart was jumping! We went out to dinner, and at one point, noticed one of his "friends" that happened to be a girl, was a bit more than a "friend." Sure, he didn't seem interested in her, and explained later that she was "nuts."

Year 2: we continue our talks, which are now as often as 4 times a week, and I start developing feelings for him. We talk about life, funny things that happen to us, and relationships from our past. He invites me to his birthday gathering with some friends, where (while he is in the bathroom) they sneak in that he is currently "seeing someone", and she lives in another country. I take it with stride, because, again, we're not a couple, so why does this matter to me? When I talk to him about it, he denies he knows what they are talking about. I don't press about it, because I'm not his girlfriend, so why do I care?

Year 3: Our friendship deepens. We now talk every day, and then he starts talking to me about a new girl he quickly fell in love with. I didn't mind, because I myself was in a relationship, which he knew about too. I was there for him when he started dating her, and was there for him when he realized she turned into a lesbian and eventually, dumped him for a woman.

Year 4: We talk every day, jokes get to be a normal part of our friendship, and sarcasm is a daily thing between us. In the midst of his break up, I am there to help pick-up the pieces, and he eventually finds another girl to help heal the "pain." I sit by and watch, as I already know this isn't going to end good. I watch him squirm over this new girl (a singer, who happened to be beautiful) and witnessed her use him. He comes to, and realizes the same thing months later. During a "break" for both of us from significant others, our phone conversations get...for lack of a better word, "sexy." I'm "ok" with it, but at the same time, I don't want to move forward with it and have it become physical, for fear of ruining the friendship, and becoming one of his "girls." I end the conversations, and we don't bring it up again.

Year 5:

I am back with my ex-boyfriend (who live 250 miles away), and he is trying to make things work with his on-and-off girlfriend (who lives over 5,000 miles away.) Unfortunately, his relationship goes rocky, and at the same time, my work situation becomes unbearable: I quit, and he is the only one who helps make it all better by talking me through it.

Summer becomes fall, and in those "I'm not so busy" months while I transition into a new job, him and I are inseparable. We go out constantly, seeing each other every weekend, Fridays, Saturdays, even Sundays. Late night outings become regular, and one (of my VERY drunk nights) we go back to his place, and I plop down on his bed, drunk, and possibly start snoring minutes after. I know, SEXY, right? He then proceeds to start spooning me, and, his hands suddenly start becoming interested in exploring my body. I, of course, end it because "I have a boyfriend!", I told him as I left his apartment. The next day, he calls me early in the morning to see how I was feeling. Things get weird between me and him, and he notices it. When we see each other again, our goodbyes become long hugs, and staring into each other's eyes. I don't talk about it, and neither does he...so the moment fades.

Things finally get back to normal, and he finds a new girl to pay attention to. I sort of feel a pang of jealousy when I find out about the new girl, especially because we had been spending so much time together, and now I had to compete for his attention. The night I met her, I tried to help him get on her good side, and, without her looking, he did put a hand on my knee for an extended period of time; which really confused me. They continue with their romance, and I sit aside. They end up breaking up, of course.

Year 6: he meets a new girl, who, I know, is not meant to last. I tell him this, because of things she does at the beginning of the relationship, but he moves forward with her anyway. Now they are 1 year into their relationship, and unhappy as ever. I myself, am not happy in the relationship I am in, and after much contemplation, am planning to have the break-up conversation with my boyfriend when he comes to visit.

So, I guess my question is, with my looming break-up, and his break-up close too, should I tell him I have feelings for him? After 6 years, I know I love him, and we've said it to each other a couple of times. I can't imagine trying to date new guys, and still have that "what if" feeling about my friend. I can't imagine sharing my feelings with a new guy and my best friend; I'd really rather not do that.

What do you guys think?

View related questions: at work, best friend, drunk, fell in love, jealous, lesbian, my ex, period

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A female reader, wonderbread United States +, writes (22 February 2013):

I'm going to make this short because I think this quote applies:

"Nothing ventured, nothing gained."

At least that's the vibe I'm getting off of hearing what you have to say. He has show his interest, time to show yours :)

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A female reader, oldbag United Kingdom +, writes (22 February 2013):

oldbag agony auntHi

I think yes,you should tell him. 6 years is a long time and you both have a string of failed relationships with others during that time.

The only thing you haven't done is have sex really.Tell him how you feel,could be he is just waiting to hear it.

If he responds with just wanting to be friends, at least you will know where you stand.

Good Luck

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A female reader, anonymous, writes (22 February 2013):

It's so obvious that you could show him your feelings and they would probably be reciprocated that I am more concerned about why you are asking us for 'permission'.

If you think it could ruin your friendship forever, with or without some sort of relationship that may or may not last, then is that worse than never knowing? It seems unlikely that he's going to reject you and you seem like the only woman that he can really talk to and whom he trusts. What's holding you back? Do you wish that he'd made a move on you a lot earlier instead of seeing other women?

If so, it sounds like he needed time to mature anyway and to just date around a bit until he understood more about himself and about women.

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