Is It Okay To Work With My Ex, Even If My Boyfriend Objects?

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Is It Okay To Work With My Ex, Even If My Boyfriend Objects?


Dear Chantal,

What are your thoughts about working with an ex?  My ex (Troy) and I dated for 4yrs or so. He has a home renovation business, where I often lend a hand doing various jobs from administration to actual projects inside homes. Side note – I love this work. I have a background in interior design, and the team there is amazing.

My current boyfriend (Kevin) is wonderful to me, and I love him so much.

I finally found myself a caring, thoughtful, long term thinker, thanks to you and your books! (I bought No More Assholes after my last breakup, and After The First Kiss when I found this new man. I love your advice, it’s absolutely worked wonders for me.) His argument is, he wants us to move forward “as one” and doesn’t see how we can do that if I continue to work the odd time with Troy.

Learn how to use the vetting process that weeds out selfish, short term thinkers.


He believes I’m holding onto to something, but I absolutely am not.

The fact is, I love what I’m doing and I have the flexibility to choose the days that work for me to help Troy. I’m also looking to start my own business, and my boyfriend Kevin and I have purchased our own truck and some tools and begun doing work around our home and even odd jobs for other people. I do think it’s important to learn and network from fellow individuals in this field, gaining the education and experience I’ll need to be successful in our company one day.

Kevin has read texts from Troy in the past that have been inappropriate or disrespectful to me or my relationship.

I asked Troy to stop that behaviour…and he listened! He has been “work only” ever since. It’s been very nice because I want to be respected and taken seriously. One of the reasons I left Troy was because he was very disrespectful, discouraging, and negative. But now that we aren’t together, and haven’t been for 2 years, our working relationship has become healthy. I am in no way shape or form considering the idea of getting back together with him, even if my current relationship failed.

And I have to say, Troy feeling like a complete turn-off to me is a result of being in this healthy, mutually respectful relationship with Kevin. Even if we don’t see eye to eye on something he always makes an effort to communicate… a lot! I never grew up in a household where arguments could become constructive, where we learn and share each other’s points, but this is another trait I really admire in Kevin. This is why I believe Kevin is reading too much into Troy and I “occasionally” working together.

Plus, Troy has been dating someone seriously for some time now, so Kevin should understand that we’re both past each other and have moved on.

That being said I also feel that I shouldn’t have to give up something I enjoy doing and make money at, just because Kevin feels threatened or insecure about the odd times I work for Troy. I’ve told Kevin I won’t be giving up working there because I enjoy it and I make good money, but I do wonder if it’s worth it.

I hate upsetting Kevin, though I’m aware that part of me is sticking to my guns because a man would never be asked to give up something he was earning good cash at and enjoyed, right?

I want to add that Kevin’s last relationship ended with his significant other being unfaithful. I am not sure if he has really dealt with those feelings yet, and am suspicious that part of his issue comes from wondering if I’ll do the same thing to him.

Can you help me figure out what’s right in this case please? I don’t want to miss out on something for a man, but I don’t want to lose a good man, either.

Sabrina V.



Dear Sabrina,

It’s the age-old question; how much should you let jealousy form your behaviors? Should you let your feelings affect how you treat your partner? Should you let your partners affect how you live your life? It’s a tough question to answer, even on the best of days. We all want our feelings to be respected, and when it looks like a win for one is a loss for the other, who should win?

Ideally, jealousy would never play a hand in dictating what happens in someone’s life.

I’m speaking from experience here since I had my own battle with that very emotion not too long ago. See, I picked a man who had an ex in the picture, because his intent as a father was to co-parent, and co-parent well. So while his kids were young and tender he did everything he could to make sure they were happy, which meant making sure their mother was happy, too. That’s a tough pill to swallow when you want your significant other all to yourself.

But we can’t go around trying to own people.

What we need to do is find the sort of partner we can trust, and love them enough to let them choose the life that’s best for them. Compatibility means finding someone whose decisions we can live with, not someone who’ll modify themselves to fit our comfort zones.

Yes, our partner may make decisions that make us squirm inside. But when you look past your emotional discomfort what do you find? Are their behaviors what I like to call “worthy”? Or are they selfish?

Selfish behaviors, the sort that lends to feelings of jealousy and knee jerk desires to control one’s partner, are the ones that revolve solely around a person’s sense of gratification. If he or she does things like exchanging sexy texts or sneak around behind your back because they like all the extra attention, then you’re right to feel jealous. It’s human nature to seek the devotion of our partners, and I’ll back you up if you decide this sort of person isn’t right for you.

But worthy behaviors can trigger us too, and they’ll bring about unnecessary feelings unless you take a step back and assess why you’re unhappy with traits that actually show good qualities in a partner.

Sure, my husband being a good dad meant his ex was front and center for a number of years. But is it okay for me to make a fuss and ask my man to distance himself from his kid’s well-being? That answer is “No”, and if I want to keep him I need to make sure I’m caught up on my meditation minutes so I’m not over-reacting to his good deeds with fear and anxiety.



So what does working with your ex say about you? That you’re ambitious, forward-thinking, and able to see opportunities for growth without letting old news get in the way. But Kevin does have a valid reason for having negative feelings towards Troy, and you should acknowledge that he’s right about not trusting Troy, even if he should be trusting you. But on that front, kudos to you for nixing Troy’s bad behavior in the bud, and to Troy for listening to what you need in terms of respecting your relationship with Kevin.

But because the line has been crossed once before, I suggest letting Kevin look at how you’re communicating with Troy any time he wants to.

Those with nothing to hide, hide nothing. Given that the best predictor of future behavior is past behavior, letting Kevin see a growing amount of respectful, business-only discourse between you and Troy will help ease his mind.

Should Kevin bring up his feelings again let him know you care about him and how he feels matters to you. Listen to what he’s saying about what makes him feel insecure, and you can use my “What Else” exercise in Fix That Shit to help get all his concerns out, so you can then talk about solutions together. In this case, you want extra money and flexible hours along with an environment that’s educational, so ask him if he feels there are other sources for that. If this is more about what you gain than working specifically with Troy, be flexible on the possibility that you can achieve your goals in other ways.

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And last but not least, be sure you’re using my #1 relationship rule – it’s not fair to ask for anything you’re not willing to do first. If this scenario was reversed, would you be okay? If the answer is yes then see if you can negotiate with Kevin. But if the answer is no, you’ve got some work to do. Either you need to become more secure yourself so you can lead by example, or end your work with Troy so you can find opportunities that won’t clash with your own values, just because you want to be selfish.

Great relationships are all about playing the long game. And if that means sacrificing one marshmallow today so you can earn two marshmallows tomorrow, then a loss in the near future really can be a winning scenario on the long run. But the key is choosing the right man, and practicing love as a Verb – found in the things you do to help your partner be happy.


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Chantal Heide – Canada’s Dating Coach

Chantal Heide is an Author and Motivational Speaker, focusing on dating and relationship building. Her books Dating 101, Comeback Queen, Fake Love Need Not Apply, No More Assholes, After The First Kiss, Fix That Shit, Say Yes To Goodness, and Custom Made (available on this website, Amazon, and your favorite online book retailer) help her readers attract the love they’re looking for, regardless of their starting point . View her BOOKS page for more information. Be sure to check out more free advice on Facebook, YouTube, and Itunes, as well as fun tidbits about her life on Instagram and Twitter.

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