Counsellor,

I’m in a tricky situation and could really use some advice. I’ve developed feelings for someone, but there’s a big catch—she’s the ex-girlfriend of one of my closest friends. They broke up about a year ago, and since then, she and I have become good friends. Over time, those feelings have deepened, and now I find myself wanting to ask her out. I’m struggling with how to handle this because I don’t want to hurt my friend or damage our friendship. He’s moved on and is dating someone new, but I still worry that he might feel betrayed or uncomfortable if I pursue a relationship with his ex. At the same time, I can’t ignore my feelings for her, and I think there could be something real between us. I’ve been going back and forth about whether I should talk to him first or just let it go. Part of me thinks he might be okay with it, but another part worries that this could create tension between us. I value our friendship, but I also don’t want to miss out on a potential relationship with someone I really care about. How do I approach this situation without causing harm? Is there a right way to go about dating a friend’s ex, or is it something that should be off-limits entirely?

Being adults should mean you’re all able to deal with things in a mature way. Yes, there’s a right way to approach this. The fact that you’re asking for advice says you’re likely a decent, mature person. If your bonafide friend is also a decent, mature person, he should wish you and her well. And no, dating a friend’s ex isn’t automatically off limits. It’s good that you value his friendship, but if this is a possible lifelong partner for you, don’t easily toss the opportunity away.

Certainly, talk to him. You want to give him a heads-up on the fact that you have feelings for her. He may want to know if anything was happening before they broke up. And you can’t blame him if he wants clarity there. You’ll want to give him a rundown of how things developed between you two, just out of respect, to make sure to shut down any inclination that there might have been cheating. The probability of his feeling betrayed or uncomfortable may be slim, but it’s possible. However, he’ll get over it, if he is mature and a real friend.

My advice:

Talk to him: Ask him for any information regarding risks or benefits. See if there’s more regarding why they really broke up. If there’s nothing shocking, and he’s good, then you’re good to go. If he’s not good with you dating her, then you’ll have to make a decision. If you think he’s being immature and petty, then tell him that, and you make the call. If you think she’s “the one” and he’s being unreasonable or seems jealous, then assure him of your continued friendship, but let him know you’re going forward with her. But if he reveals something serious, then evaluate, verify and act accordingly.

Speak to her: If you do decide you’re making things romantic, let her know you respect your friend and that you spoke to him about it. You also want to give her an opportunity to share anything regarding that relationship. There may be other information that she can offer. #BothSidesMatter

At the end of the day, this is your call. You’ll have to evaluate based on all the information you gather. And when you make a decision, don’t regret it. Work things through as best as you can, no one can ask more of you, not even you. You can always reach me at
counsellorscouch.com.

Get on The Counsellor’s Couch with Rev Christopher Brodber, who is a counsellor and minister of religion. E-mail questions to allwoman@jamaicaobserver.com.