Asking for a friend: Help! Is it okay to date my BFF's ex? Advice for your toughest problems

  • Do you have difficult, embarrassing or awkward questions to ask? Submit them anonymously and 'Friend of a Friend' will do their best to help you out
  • In this week's column, we answer questions about what to do if you have a crush on your friend and how to help your pal left out by the 'cool kids'
Amalissa Hall |

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What do you do when you have a crush on your best friend?

This column is here to answer all your difficult or embarrassing questions about being a teenager. If you’ve ever wanted to know how to overcome particular situations at home, school, in your social lives, or even in the animal kingdom, our “Friend of a Friend” is an expert to help provide answers for you!

Do my parents like my sister more than me?

Dear Friend of a Friend,

My older sister has come home from uni to stay with our family. I love having her home as she is my closest friend. She is an extremely vibrant, humorous, extroverted and sociable person. 

But I’ve noticed that my parents have a better relationship with her than they have with me. Ever since she has come back, they seem to be much happier. They both no longer seem so stressed at the dinner table as they did with me because my sister can make them happy. 

I’m upset that I can’t do this for them on my own. I feel insecure, as if I have not lived up to “perfect daughter” standards. But I don’t want to change myself just so they are happier around me. How can I lose my insecurities surrounding this? 

Signed, The Other Sister

Hi Other Sister,

It’s great to hear you have a good relationship with your sister, but you need to stop comparing yourself to her. It’s like apples and oranges: they are both excellent in their own way. You say she is an extrovert, but what are your powers as an introvert? 

Think about the qualities you offer that your sister may not have. Identify the strengths that make you confident about being yourself, and that will help you overcome your insecurities. 

Also remember, your sister is older, so she’s learned skills such as small talk and understanding work stress over time and through her own experiences. She most likely felt the same way  when she was your age – just ask her!

In regards to your parents seeming happier, the saying goes “absence makes the heart grow fonder”. They are glad your sister is home from university. They may be speaking to her more because they haven’t had the opportunity whilst she was away, not because they are unhappy with you! 

Let go of the idea of being “perfect”, because holding yourself to impossible standards will only make you miserable. Acknowledge that your relationship with your parents will be different, and there’s nothing wrong with that.

Next time at dinner, offer up some topics related to your interests. Your parents will  appreciate the effort, and you’ll feel more involved in the family.

Sincerely, Friend of a Friend

It's normal to have some insecurity between siblings - don't be afraid to talk about it.

I think I have a crush on my best friend!

Hi Friend of a Friend, 

I’m currently in a tricky situation. I have a best friend, who is the opposite gender to me, and we’ve known each other for nearly four years. I think I’ve developed feelings for him, due to his personality and I feel safe when I talk to him. 

However, I’m not sure whether he also has feelings for me. It’s hard for me to ask him about this because, once I do, maybe I will ruin our friendship. How can I tell if he likes me? 

Thanks, Best Friend or Boyfriend

Hi Best Friend,

I’m not surprised you’ve fallen for this boy; it’s very easy to develop feelings for someone you spend a lot of time with. Trust and safety are both important in romantic relationships, so it’s no wonder that you feel like he could be a good match for you.

If you want to know more about his thoughts without being direct, perhaps ask a trusted friend of yours to casually bring it up with him in conversation, and ask them to report back. That way you can decide if this is something you want to pursue – but the problem is that you may not get very clear information.
The best way to know for sure is to ask him yourself. I know it can be really difficult to be so direct, but if you are honest about how you feel about him, hopefully you’ll be able to have an open conversation about your relationship. 

Best-case scenario, he likes you, and worst-case scenario, he doesn’t. It will hurt to be rejected, but it would also hurt to regret not making a move! You can repair friendships with time, and if you are both willing to move past any awkwardness, then you will prevail as friends.

Sincerely, Friend of a Friend

Tips for problem solving and staying balanced 

Can I date my best friend's ex?

Hi Friend of a Friend, 

At the start of the school year I developed a crush on my classmate. A few months ago, I called my best friend to share these feelings with her (which, for me, is rather rare). Just as I said to her “I think I have a crush on someone”, she said that she did, too, and I had a sinking feeling she liked my crush. I asked her to share hers first, and my prediction was correct. 

Then, I made up an excuse for not being ready to tell her, and for the next few weeks, tried to get over him as they started dating. 

Fast-forward a few months, and they broke up. At some point, we had a conversation where she said real friends shouldn’t date their friends’ exes. It was around this period that I started texting him again.

The thing is, I could never achieve anything with him without ending my friendship with my best friend, even though I’m pretty sure he likes me now (and before he liked my friend). Should I just stop talking to him so I move on and avoid hurting anybody?  

Sincerely, Missed Connection

Hi Missed,

If you move on without saying anything, will that make you happy? I completely understand that you don’t want to make a fuss, but don’t disregard your own feelings. If this is something you (and your crush) really want, I think you should talk to your friend and explain the situation, from the very beginning, so she understands the context of what happened.

Talk to her honestly, because one of the biggest reasons for a relationship breakdown is a lack of communication.

If you reveal that you liked him early on, then she may be more understanding of where you are coming from and the confusion you are feeling now as a result of it. It seems unfair of her to hold a claim over this boy, especially since they are not together anymore – I think you should ask her to explain why she would be so unwilling for her friends to date exes. 

True friends should be able to last through secondary school boyfriends!

Best of luck, Friend of a Friend

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How do I help my friend?

Hi Friend of a Friend, 

One of my good friends has told me that they are having a tough time due to friendship problems. Basically, he and his friend have been really close since they started secondary school. They hung out a lot and did almost everything together, until recently, when his friend joined a squad of “cool people” and has been spending more time with them and leaving him behind. This has made him really sad and lonely at times. How can I help him?

Thanks, Too Cool for School

Hi Too Cool,

Unfortunately one of the sad facts of life is that friendships last different lengths of time. Some people are short-term friends, some are forever. It sounds like your friend’s friend is starting to explore different avenues of friendship.

There’s nothing wrong with socialising with other people, unless he is leaving your friend behind without much explanation. Being part of a “cool” group is definitely alluring, but there’s nothing cool about rejecting people because they don’t fit in a certain stereotype.

Luckily there are a lot of other people in  school, and your friend should try to hang out with them. He is bound to find someone with the same interests.

In the meantime, invite your friend to hang out with you, introduce him to your friends, and make him feel included!

Sincerely, Friend of a Friend

If you have a question you’d like answered (about anything at all), please send an email to [email protected] with “Asking for a Friend” in the subject line. Don’t worry, you will remain anonymous! 

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