When Should I Date My Ex-Boyfriend’s Pal? – Help Me Love Doctor

Why not send former Kingston-resident Love Doctor your relationship queries? Use the form to submit your question(s).



I split up with my boyfriend in March, but I am hotter for his friend than my former love interest. How long should I wait to date my ex-boyfriend’s good friend?

Joelle, May Pen


Love Doctor’s Answer:

Love Doctor MontiThere is no need to feel guilty about the situation. However, is this just a fling you are seeking, revenge or to suddenly be back in your ex-boyfriend’s life?

This could be a challenging potential love triangle, depending on how your relationship ended and whether either of you would consider trying to resurrect it. Should there remain unfinished business and you both remain single, then dating your ex-boyfriend’s pal will just make things messy.

Often people decide to date an ex-lover’s friend when they learn that they have moved on and are happy in their new relationship, so want to keep a close eye on them. That is not the right reason to entertain dating this man for you.

If your ex-boyfriend and this man are good friends, how would they feel about having both become involved with you? And what sort of reputation will you have if you start dating your ex-boyfriend’s friend so quickly after your split? Would you be devastated if your ex-boyfriend never spoke to you again?

Time is the only healer for a broken heart. My advice is that the longer that you wait to potentially date his friend, the better.

I appreciate that you may be getting completely mixed signals from your ex-boyfriend’s pal, which you may be mistaking for romantic interest rather than pity.

You need to first establish whether this man has any interest in you, check that he is single and that it is not just lust for either of you – because that will cause chaos and arguments between the three of you. You are currently vulnerable and you certainly don’t want to just be used for his sexual needs.


My suggestion is to talk to your ex-boyfriend’s pal to discuss the situation, and if there is a chance of genuine romance seek a second opinion from someone who knows both of you.

Rebound relationships tend to fail and leave both parties regretting these, usually asking their closest friends why they didn’t tell them not to enter the doomed romance. Go grab some vital advice from respected friends so you don’t slip up and become humiliated.

As for when is the right time to date your ex-boyfriend’s pal, the answer is when you know it is a relationship that can develop. Another reason to delay this is to not hurt your ex-lover’s feelings.

My advice is that rather than sneak behind his back, because he will eventually find out, is that you both need to speak to him about your budding romance.

This is because the subject covers not just his relationship with his close friend, but also your relationship with your him. Like it or not, if this romance lasts then you are going to have to maintain some form of relationship with your ex-lover.

You both need time to move on, and having each other becoming a constant in each other’s lives again makes that difficult.

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