Reject a close friend interested in dating me?

Question

I recently went through a pretty rough break-up with a long term boyfriend. I've been feeling a little better about it recently and my friends have noticed.

My problem comes in with one friend in particular. Let's say he's Bob. Bob recently confessed to me that he has been attracted to me for about two years now. We talked about it for a little bit and I explained (poorly) that I was still reeling from the break-up. We dropped the topic.

Please note I don't want to be with this person in any capacity beyond a typical friendship. There's no reason for it other than I'm not attracted to him or interested in him in any way beyond the relationship we already have together.

After the confession, he's been trying to spend time with me one-on-one. Tonight, Bob asked if I wanted to go to dinner with him and I invited a friend to come along with us. It's important to note that the other person I invited is someone I'm very close with and previously had had a casual relationship with, but for many complicated reasons, is never someone I would end up dating seriously. He and I are very comfortable with each other and will often give each other long hugs and/or cuddle pretty openly. We've also kissed very briefly since the break-up.

After dinner, the three of us leave and hang out in a common area for a little while. The third friend (a little bit drunk) is very close to me during this time and pulls me into hugs and leans his head on my shoulder and such. He then goes to bed and leaves Bob and I alone. Bob asks me why I'm so close with this third friend and why I've been going on so many dates with people from an online dating app I've been using. We have a bit of an indirect conversation about it, but it seems very awkward and I didn't give any satisfactory answers.

Towards the end of the night, he asks if I would want to lay down with him for a little bit, in a purely platonic way. I politely decline. He also keeps offering to let me sleep in his room because at this point it's past 4am and I still needed to drive home. I graciously decline these offers as well.

I need a way to explain, directly and honestly, with my friend that I'm just not interested him as anything more. I want him to understand that I really, truly am still reeling from the break-up and that I'm not looking for anything real or serious. I'm using these other things as (admittedly poor) coping mechanisms and that's the extent of it. I'd also like to avoid discussing my relationship with the third friend if I can. I want Bob and myself to be able to be friends afterwards and still have the same relationship we've always had, but I don't want it to be awkward between us either. This whole situation is making the process of getting over the break-up a lot more difficult and making me feel really guilty over the whole thing.

Answer 1

I suggest you clearly tell him you are not interested in a relationship with him. And tell him you will never be interested in a relationship. He should clearly know that there is no point in hoping it will every happen.

If you use any explanations like you are not ready now or you have to get over this or that or maybe this or that he will have hope and he will continue to try. You won't like it and he will be disappointed trying and he will be disappointed if he tried for months and still has no success.

If you tell him one time clearly that you are not interested then that might hurt him but he will get over it. And when he accepts reality then life can go on normally for him and you.

Don't postpone the inevitable. Tell him you are not interested and won't ever be interested.

I give you this answer from personal experience on the receiving end of "I am not ready yet". I tried and had hope and more hope and because she didn't want to say no she told me something like "maybe". I interpreted her maybe as "almost sure it will happen" but I am pretty sure she meant her maybe as "99% sure it won't happen, but I don't want to tell you so clearly". In the hindsight she should have told me: Forget it, it will never happen.

Answer 2

There's a problem (and I suspect) an impossibility here. You want:

I need a way to explain, directly and honestly, with my friend that I'm just not interested him as anything more. I want him to understand that I really, truly am still reeling from the break-up and that I'm not looking for anything real or serious. I'm using these other things as (admittedly poor) coping mechanisms and that's the extent of it. I'd also like to avoid discussing my relationship with the third friend if I can. I want Bob and myself to be able to be friends afterwards and still have the same relationship we've always had, but I don't want it to be awkward between us either. This whole situation is making the process of getting over the break-up a lot more difficult and making me feel really guilty over the whole thing.

This is directly contravened by what you need to do. If you never want to date him, the moral thing is to tell him that as clearly and unambiguously as possible so he and you both know where you stand. Especially since you two know each other for so long, and since you seem to value him as a person, it is the moral and ethical thing to let him know.

Don't expect things to go back to normal between you two, however. You don't know (and can't know) how much of his friendly behavior towards you originally was geared towards eventually dating you, and you can expect that any part of that will disappear following the revelation that you're uninterested.

Now that's a very uncharitable description of Bob. Maybe he really was your friend and just caught feelings. Even then it's unlikely that you two can have the same friendship that you had previously. Getting rejected hurts, getting rejected after nursing a crush for two years hurts exponentially more and can inflict a lot of damage on a friendship. More likely then not, he'll get the message that you don't like him much (well duh, but decoupling friendships and relationships like that doesn't work if you have a crush).

I've never seen this work when it's been going on so long, among at least a dozen occurences within my friend circle. Almost always the two involved stop talking and hanging out after this. When feelings build up for a long time like this it's very hard to let those go and much harder than if for instance this happened a couple of weeks into getting to know each other. This isn't to be too pessimistic, but you most likely will not be getting back to where you were before.

Answer 3

I tried adding a comment to Edgar's answer but it ended up growing too long.

In addition to telling him that you aren't/won't be interested in him, you need to need to make it clear that you still want him in your life. When you do so, try to avoid using the word "friend" as in "I like you as a friend." This has unfortunately emerged in pop culture as the friend zone, seen as an inescapable prison for nice guys who deserve the girl who is too foolish to see their value.

Instead explain to him that he's an important part of your life as he is and the fact that he's blatantly ignoring your boundaries not only looks bad on his part, but also causes more hurt for you. Let him know that he's an important part of your life and that you need him to be there to help you rather than put his own interests ahead of yours. Try to avoid ultimatums, but if he refuses to accept what you say, you may need to make it clear that, even though it hurts you, you can't have him in your life for a time if all he's going to do is try to make advances on you.

Even if your conversation goes fantastically, things will change. You may see a bit of an absence from Bob while he comes to terms with it but hopefully he'll come back with a better understanding of how you two fit together.