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#62 - Is it right to date him?

Hello,

Two rather similar problems so I've put them together.

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Problem Child #1

So basically in like 8th grade, my friend went out with..let's just say, J. Now, she has a guy that wants to date her, but he and J are best friends. J has admitted he still has feelings and wants to go out with her, but the guy she wants to go out with doesn't want to hurt his best friend. 

My friend and J's bestie would be brilliant together, but J lives down the road from her, so they constantly hang out, making it it seem like she doesn't want to go out with the other dude.

What should I tell my friend to do? Also, how can she let J know, without damaging their friendships?

Thanks.

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Problem Child #2

So there is this dude. [I don't know if I like him. He likes me. We are really close friends and I've told him a lot of stuff, and I really connect to him, but I don't know if I like him. But I don't want to do a 'trial' relationship, because I would hate to break his heart]. I would date him, but there is this problem. 

He's my friends ex. When I had a fight with a friend, she tried to use the key argument of I would go out with her ex, I'm a bad friend etc??

But I really like him. I don't know what to do you know? It was a bad breakup, so she's really sensitive still.

HELP ME!

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Heya, my two problem childs. 

I'd first like to point out to Child #2 that I've put part of your problem in brackets because it completely contradicts what you say at the end. So basically I'm going to ignore it lol, because I don't think it's the main issue.

For Child #1, I will refer to 'you' as if you're the one I'm advising even though it's for your friend simply for the sake of convenience.

Anyway.

Let me try and recap both your problems. You both want to date someone that is out of bounds because you either dated his best friend before or your friend dated him before - and they both seem to have some feelings left for them. 

There's never a way to escape such situations without hurting anyone. I'm so serious; someone will get hurt, but it's now for you to decide what you want. 

The truth is, this is the type of situation where you have to choose between yourself and a friend. Do you want to pursue the relationship and make yourself happy, while possibly losing a friend? Or would you rather suppress your feelings and live in the pain of bottling things up, so that you can preserve your friendships? It's a decision you have to make yourself, really. Even I can't make that for you.

Instead, I'll just tell you stories and hopefully they help you decide. 

Some years ago my friend (let's call her Cecily) had been dating this guy, and it had been a long time - like say two years - until it ended because he cheated on her...with her really close friend, let's call her Gwendolen. It was a bad and messy break-up, and of course it allcaused tension between Cecily and Gwen. They stopped talking, and Cecily couldn't stand to be in the same room as Gwen. Still, Gwen decided to pursue the relationship with him further. 

From where I saw, they seemed so happy. Gwen and he looked like a better couple than he and Cecily, so all of us seeing us together was so conflicting because Cecily was in pain, and we were just watching her suffer, yet Gwen was having the time of her life with him. It was basically the happiest we'd seen her. 

Basically, Gwen chose herself over her friend, Cecily, and she ended up finding lots and lots of happiness. Of course, as time went by, Cecily had to accept that that was the reality and she slowly healed to the point where she could actually hold a conversation with Gwendolen once more. 

My problem childs, if you decide to choose yourselves and pursue the relationship, you need to be prepared for the worst while also hoping for the best. You are bound to hurt some people along the way, but if you and that other person are truly happy together, then perhaps you might find that it was worth it. It will also force someone like J, who still likes you, to move on. 

However, you could choose you and unfortunately loose everyone. This especially goes to Problem Child #2. If your friend is really sensitive about the break-up, I reckon it'll be extremely awful for her best friend to date the guy who she not only loved, but the guy who also left her heart-broken. Personally, I would choose her over myself because I'd hate to go through what she would feel if that was the case. But then again, I don't know the extent of feelings you and he have for each other, and if you feel like you do really, really want to go out with him, then do so. But I will warn you that it could get particularly messy.

I think Problem Child #1 is in a better position to date the guy, but again it might get a bit messy with J. Also, if J's best friend is not willing to date you because of his friendship with J, then I guess it can't happen, but I also think that you should try and talk to J about how he would feel about you dating someone else (you don't have to say who), and whether he would be mad if you liked one of his friends. You say you hang out at J's house often, so you could ask those as hypothetical questions during this time. 

I do think that it's a much-needed conversation that you need to have with J seeing as he still has feelings for you. You need to talk to him about how you still do care for him very much, but as a friend now, and you would like him to start the process of moving on. If you get things cleared up with J, then maybe the situation will be a bit clearer and you'll be able to decide whether you and J's best friend should go ahead. Perhaps J's best friend should also talk to J as well about it, because sometimes feelings are things we can't control and have to pursue them in the end because the worst thing is having regrets. 

Again though, to both of you, it's a choice I can't really make for you but that you have to make for yourself. It's annoying yea, but it's for you to weigh the costs and benefits of the decisions that you will make. 

Hope I helped. If anyone has something to chip in, don't hesitate to do so!

Lots of luck and love,

- genie_us xx