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Transitioning from Best Friends (13 years) to Dating

Tagged as: Dating, Friends<< Previous question   Next question >>
Question - (3 August 2010) 4 Answers - (Newest, 5 August 2010)
A female United States age 41-50, *ostinSpain writes:

While I have always felt an attraction to my best friend, we have never really considered the possibility of him and I being more than friends. See, we've been best friends for 13 years now and have the same small circle of friends, which include his brother and sister-in-law.

A few weeks ago, our group of friends all went away for the weekend together. He and I were sharing a bed and while this isn't the first time, it was different. On our second night, he was goofing around and taking up the whole bed. I was tired so I just curled up next to him and went to sleep. At some point, he covered me with a blanket - something he's done before so it was fine but then he wrapped his arms around me (we were facing each other), pulled me closer to him so his head was resting on my head, intertwined his legs with mine and fell asleep. I woke up to realize we were CUDDLING! This was strange to me but it felt amazing so I went with it. At some point though, I became uncomfortable and rolled over on to my other side. Again, he pulled me in close to him, intertwined his legs with mine and since I was still in him arms, he reached his arm out to my outstreched arm and was holding my hand. We slept in this spooning position all night!!!!! I woke up the next morning not knowing what to think so I just let it go for the time being.

Following weekend, he came over to my house for dinner and then we went to see a movie. Since he and I are the only single friends left in our group, it's not unusual anymore for us to hang out just him and I. During the movie, we held hands and I rested my head on his shoulder. I didn't think anything of this as we are more cuddly than most friends are - we often curl up on the sofa together to watch movies at home, sit close together, etc. But then after the movie......Before the movie, he wasn't going to stay at my place (I live 45 mins from him) because he thought he had to help a friend with something the following morning. However, after the movie, he hadn't heard from his friend so he decided he was going to stay so he came back to my place and we ended stayed up most of the night talking and drinking a bottle of wine. Around 4AM we went to bed. As we lay in bed, he on his back and me cuddled up in his arm, we started to talk some more. It was a little weird to be cuddled up with him again so I asked him if he had ever thought about whether or not we could be more than friends. He said he didn't know. He had never actually thought about it before. We then laid there in silence for a few minutes before I finally just lifted my head enough for our lips to touch (I told you were were cuddled up). At this point, we gently kissed and eventually our gentle kisses turned into a steamy make-out session. We finally fell asleep sometime after 6AM and again cuddling together. When we woke up later that afternoon, we had another 1 or 2 hour make out session (I think I initiated that one). We then had lunch and hung out until he had to leave to go help his friend.

We never did talk to each other about what had happened. I was REALLY confused though and over the next week, I spent a lot of time trying to sort out how I really felt. We hung out later and the week and realized we were going to have to talk about it. So this weekend, we made plans to hang out again and after a day of minigolfing, dinner, and a movie at his house, we decided it was time to talk.

We spent 3 or 4 hours talking and while I'm pretty sure I'd like to take the leap and try dating, he's not so sure....to be fair, I have been thinking about this longer than he apparently has. Also, in general, I tend to be a risk taker where he tends to be more cautious.

Keep in mind that as we are having this LONG discussion, he's sitting on the sofa and I'm laying across him while he's holding me in his arms.....we're like that the ENTIRE conversation (except the one section of the conversation where I've noted).

We've both said that we are each other's best friend. We've also both said that there isn't anything we wouldn't do for each other and that we can't imagine our lives without each other (we lost contact for 3 years right a few years after college and don't ever want that to happen again).

We are both really scared of losing our friendship if things don't work out.

He also has this issue with experience. He got a late start into dating (he didn't have his first kiss till he was 24) so he for some reason that I don't understand kept talking about how I have had all this experience and he hasn't. He's dated a good bit in recent years but he's never had a real relationship nor been in love (I have been in love twice, engaged once). I tried to explain that experience is relevent - that it's based on personal growth and learning and that I had to have my experiences in order to get to where I am today where he is a different person and therefore doesn't necessarily have to have the same experiences.

We also discussed that we don't ever want to hurt each other. While we'd never do anything to intentionally hurt the other one, it's a risk you take when you get into a romantic relationship. He said he wanted to protect me from getting hurt. ?????

When we specifically discussed the kiss, we both agreed that it was a little weird. Afterall, we've been friends for 13 years. I said while it was weird, I also kind of liked it. He said he kinda felt like he was kissing his sister but that I was also a great kisser. ?????? He said he was having a hard time seperating the two feelings and wasn't sure how to get over the awkwardness.

We talked about kissing again but he asked if I'd be okay if maybe we didn't for now....until we figured things out. Of course, I agreed.

We then continued talking and he was shocked when I said that I had always felt something for him. He said he never thought I could've or would've felt more for him so he's never thought about more with me.

We then talked about 2 girls he knows now that he's interested in but whom don't ever have time for him (remember - he's not very experienced). This is where I separated myself from him, put my best friend hat on and we had a discussion regarding girls - girls ALWAYS find time for guys they are interested in.

I told him that even if we decided not to date, we'd still be best friends but that as his BFF I felt he deserves to be with a woman who wants to be with him. The girl who he ends up with should always be willing to make time for him, treat him right, and be deserving of such a great guy. I meant it too. He was again shocked to hear me say such things as 1.) he never knew that's how I felt; and 2.) no one has ever said those things to him.

A while later, after period of silence, he leaned over, wrapped his arm around mine, put his head on my shoulder and told me that while he was really confused about a lot things, one thing he knew for sure was that he loved me. HUH?????

I didn't even ask what he meant by this as by this point we had been talking for several hours and it was late. Instead, I broke down into tears, told him I loved him too and we hugged each other even tighter. Shortly thereafter, HE gently kissed me. There was no make out session this time, just small, gentle kisses.

I pointed out that I didn't think we were going to do that and we stopped but there were more kisses later and again when I finally went home, there was a long hug at the door and he kissed me again.

I again pointed out that I didn't initiate the kissing that time. I wanted it to be clear that I was respecting his wishes. I didn't want to seem like I was pushing him in to making a decision.

Now, I think I'm even more confused than I was before this conversation. At the beginning of the conversation and up to the point where we decided we weren't going to kiss, I was pretty sure I wanted to try dating and he was pretty convinced he wanted to not date. However, by the end of the conversation, he wanted time to think more about things and now, I'm not so sure I want to date. I definitely have feelings for him but it was also clear in our conversation that he's got some things to work out.

For one, I refuse to be just an option. He either wants to be with me or he doesn't. I refuse to sit around, have him try things with these other 2 girls, have them reject him and then have him decide I'm good enough (yes, I told him this and he said he'd never do something like that to me).

Second, he needs to deal with this whole "experience" issue he seems to be hung up on that I don't understand.

But then again thinking about it, we pretty much already are dating except for the physical stuff (kissing, sex). We go to movies, golfing, camping, dinner, dancing, we cuddle, etc. Dating really isn't that big of a leap for us...it's just a matter of getting over the weirdness of the physical stuff.

Anyway.....anyone have any thoughts, ideas, suggests? Anyone ever been in this situation? If so, how did you get over the weirdness of feeling like you were kissing your sibling? How did you handle sex (OMG - we haven't even gotten there but I can only imagine how weird that's going to be)?

I keep telling myself that if it's meant to be, it'll be but that's a whole lot easier said than done.

View related questions: best friend, engaged, kisser, kissing, my ex, period

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A female reader, LostinSpain United States +, writes (5 August 2010):

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

Thanks for your responses everyone.

Update: so today he said "the whole situation is confusing. however, i just want the end result of you being my friend...."

So, I guess that's that. ????

Question now is how do I deal with it? I feel like such an ass and I'm hurt. I truly feel in my gut that he likes me in the same way I like him but......all I can do is go with what he says and right now, it sucks my heart is broken as I thought for sure this was it.

I know that if it's meant to be, it'll be and maybe later, after he's had time to process things and work on his issues (it was clear after our discussion that he's got some things he still needs to work out), things will work out. But for now, how do I go on being the best friend, watching him date/sleep with other women, etc. while I feel the way I do for him?

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A male reader, dirtball United States +, writes (4 August 2010):

dirtball agony auntWhat an awesome story. The way I see it, you are already dating. Here is one thing I can say with near absolute certainty. He likes you, and had DEFINITELY thought about being more than friends with you. He was not being fully honest in that regard. Men don't go on dates (that's what you've been doing), or spend the night in bed with women that they don't have an attraction to. The fact that you two spend so much time together is a clear indication that he's attracted to you, even if he doesn't want to admit it to himself.

What I think is happening in his head is very much the same as what is going on in yours. He is likely overwhelmed with emotions that he's been repressing to maintain the friendship.

Here's what I see going for you. You already know eachother very well. That's an awesome start. The biggest positive is the fact that you communicate so well. The number one indicator of a successful relationship is communication. The last statistic I saw on it stated that 85% of couples with relationships based around communication (versus sex or physical attraction) lasted. Strong communication is an indication of intellectual compatibility, which becomes more and more important as the physical stuff fades through the years. You also like spending time together. That's obvious, but worth stating. You feel safe with eachother. How else would you be able to sleep in eachothers arms and feel completely comfortable. Another good sign is that when you were spooning, he went for your hand, instead of your breast or something else. This shows affection rather than purely sexual attraction.

About his hangups, he'll have to decide if the risk is worth the reward, but my guess is that he wants to be with you. The thought of losing such a dear friend is paralyzing him. I can tell you from personal experience that the thought of losing someone who means a lot to you can be devistating, and it often leads to inaction if the present is "good enough" to not be worth risking. I wish I had the courage to tell my friend how I feel about her, but I'm afraid it won't turn out like it has for you, so I do nothing, just pretend to be her friend, when deep down I want so much more.

My other suggestion is to take your time. It sounds silly because you've known eachother for so long, but just because you decide to try being BF/GF, it doesn't mean you have to rush into sex. Get comfortable kissing and making out. Revel in it. Let it come when it feels natural.

Lastly, when he told you that he loved you, my gut tells me he wasn't lying. He's likely wanted to tell you that for some time. That is also something that you can point to as a reason for you to be together.

I think you two have the potential for a wonderful and lasting relationship. I hope that it works out for you, I sincerely do. I would love it if you keep me posted as to the outcome here. Best of luck.

DB

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A male reader, anonymous, writes (4 August 2010):

I envy your position (and his).

How cool is that if it works out. Best friends becoming couple.

But the risk is high though that if things don't work out and you lose an important friendship (13 years!). I think he may see your friendship as the best thing since sliced bread and scared of losing it. And he's as confused with these conflicting emotions as you are.

Don't overanalyze it. Let it flow and see where it goes but be ready to salvage the friendship--something like that is not easy to find.

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A female reader, anonymous, writes (4 August 2010):

I had a situation that's a bit like a mini-version of yours. I was friends with a guy for most of my life, but I was never attracted to him mentally or physically; our goals in life did not coincide. He began pining after me and didn't tell me for two years, and when he finally asked and I turned him down, he was devestated. And by devestated I mean he wailed about it to me for basically a year.

In fact, it was such an emotional ringer that I didn't notice one of my new college guy friend's affections. I brushed him off and we were just friends for two years. Eventually I recovered, began falling for him, probably gave too many hints, and we ended up asking each other out basically at the same time. He told me he had given up on me because he just figured it was never going to happen. We were still emotionally intimate but he had not continued chasing me because he figured he was in the friend zone. Now we're dating. I intially worried it was just physical attraction on my part. But as we've been going out, I've developed the emotional attachment less characteristic of someone with a crush and more like someone in love.

What's the difference between these situations? Well, in both of them I had a long friendship and basically had both guys in the friend zone. The difference was that the second guy was someone I was attracted to mentally and physically, and our goals in life coincided. This was enough for us to both come out of the so-called friend zone and move in to the dating zone. The foundations were always there or developed throughout our friendship - we both grew up and grew into the people we wanted to date, basically.

That's really the decision that you and your guy will have to make about the relationship - whether you were friends because you never WANTED to date, or whether you were friends in SPITE of an acknowledged or unacknowledged potential. It sounds to me like you are the second one, and your guy is realizing that he's wanted the same thing for a while too. Like my boyfriend, he just figured it was never going to happen so he never acted on it, he supressed the thought of it. After all, if he didn't think your minds and goals went well together, you wouldn't spend so much time together. If he wasn't attracted to you physically, you wouldn't be cuddling and kissing. In this case it will probably just take some time of acknowledging the idea for him to embrace it fully and begin acting on the attraction.

Here's one important thing to consider regarding the other girls. Would it ever be possible for him to open up to them the way he opens up to you? I sure wouldn't want a boyfriend that spent so much time basically dating and cuddling with his female best friend. Perhaps he's been single and never deeply in love for so long because he's always been attached to you in a friendly-but-basically-dating way, never willing to give you up for another girl. He hasn't been able to fully give himself away, perhaps, and that's a good thing because it means he's dedicated to you as a person and not just because you're his latest date.

If the mental and physical barriers regarding dating are now down because the possibilities are open, I would say just give it some time. Allow him to move at his own pace. Don't come on too heavy with the physical stuff because it could overwhelm or scare him, and don't allow any sudden advances on his part to scare you away - he's dealing with the same awkwardness. A 13 year constant in your lives is turning over.

Regarding the two problems you pinpointed: First, the idea of being an option. As I stated above, you are really in the way of these girls rather than the other way around (and this is not a bad thing!) You have the deep knowledge of him. You already occupy a good bit of his time. Perhaps due to his percieved lack of experience he thinks that you are too good for him or that you are not really interested in him - otherwise, if you wanted him, he may rationalize, you would have made a play for him by now. Once he begins to think about your relationship and allow himself to act on what you two already have, I think the other girls will really pale in comparison to you.

I had personal experience with this; the man I am now dating was after one of my friends for a while and then tried online dating but thought their personalities were not compatible although he was physically attracted to them. Once we kind of mutually brought up the idea of dating, he dropped EVERYTHING and hasn't shown interest in other girls since. One we opened up the possibilities we realized that, of all other options, we were the best for each other.

The second issue you noted was his lack of experience. Be aware that he may feel inadequate, especially around you, because you haven't dated each other (or, in his mind, you haven't picked him) for 13 years. If he felt something a ways back and pushed it down, he could have built up in his mind that you didn't care for him romantically. Now that you're expressing your desire for him you can already see him becoming bolder (kissing you) as the walls come down. I knew my guy liked me before I brushed him off, but we were never awkward as friends. Yet when he considered the option of us, the old flames came back stronger than before and we had no problem jumping into the romantic groove.

I don't want to over-romanticize my perception of your (admittedly extremely cute) story, but these are some things I've seen in my own short experiences. I can't tell you about sex because I'm saving it (personal beliefs) but what we do allow is passionate enough for me to know that it wouldn't be an issue. Note I am only 20, only knew my guy for two years and the mindsets may be very different at 30 to 35 and after 13 years of friendship. In any case, hope this helps! And listen the other aunts here; they likely know more than me!

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