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  • Writer's pictureJennifer Klesman, LCSW

Answering Your Questions About Breakups

"How do I handle him reaching out when I've set a boundary and made it clear?"

This requires complete No Contact. You’re not being heard if you’re putting up a boundary that isn’t being respected so you can’t reward or reply to any sort of contact from them. Continuing any contact, even if just to tell them that you don’t want any more contact, isn’t going to help. Acknowledging their messages at all is giving them your attention. They’re learning that they just have to continue to message you and eventually you’ll respond and if they just say the right thing, they’ll pull you right in.

If you’re already doing No Contact and this is happening, that may be upped to the next level of blocking. Typically we don’t want to block anyone, but it does send a firm message that we no longer want to hear from them in any capacity. When your boundary isn’t being respected, you’re not able to heal or get your space. If you’re currently broken up then there is little


"How do you know if you’re healed?"

Love this question! The breakup and your ex don’t consume a large portion of your mental space daily, they’ll still be there (maybe regularly, maybe just from time to time) and that is normal. However, you’re finding joy in doing other activities and spending time with other people (not necessarily romantically, friends and family count here). You’re looking forward to something in the future, or at least feel more optimistic about a future that doesn’t have anything to do with your ex. It is very gradual and often subtle when you do feel more and more healed, but overall you just feel more at peace and not so plagued by thinking about your ex.


"Why is it so hard to let go?"

This is the million-dollar question! It is SO hard to let go for many reasons. A large part of this is, feelings don’t just turn off when a relationship ends or you get hurt from your ex. It doesn’t take long for an attachment to develop and build but it takes much longer to fade due to what we emotionally invest into that attachment. The future we felt was secure now feels completely unknown. Our identities from being in a relationship to being single have shifted (and being single can feel very negative if you never wanted it). There is also time, energy, and resources all sunken into this relationship that are now gone. There is a lot of loss to grieve, a lot to transition through. Your life has completely changed and if that isn’t something we wanted, we naturally resist it for a while. Be kind to yourself and acknowledge how difficult this is and that even if it is unwanted, it doesn’t have to always be a negative thing once the grief begins to pass.


"What is the ideal first date after a breakup?"

The ideal first date is fun, light, and easy. Sure, you can go typically ‘grab a drink’ with someone or go for a walk, but do what you’re comfortable with when you’re comfortable dating again. As for the date itself, don’t bring up your ex (even if they bring up theirs), and just have fun. Go in with as few expectations as possible and be open to seeing if this is a person who you like and could have potential.

It is when you feel ready to date again. This looks like being excited and optimistic about meeting someone new, that dating seems fun to you. It is difficult to be completely 100% healed from a breakup by the time you start dating and dating will bring up memories and thoughts of your ex, so stay realistic.


"Should I wish them happy birthday?"

This can be complicated because you want to be kind and considerate, however, if the breakup and healing is still fresh, it is better to maintain No Contact. Especially if they ended it, this will show them that you are no longer an element in their daily life (they will notice). If you ended it, be careful to not give them hope of reconciliation since sometimes this just opens the door to messaging. Obviously, every breakup is different so do what you feel is best.


"How to deal with breaking someone’s heart?"

This is a great question because it really illustrates that it isn’t easy on either side of this. Whatever the reason was for ending things, you still need to focus on yourself no matter how much you care about the other person. Be careful to not give them hope if there is none and to give them space - but this is for you as well. You have your own healing and grieving to do. If you’re not already, go No Contact as well for yourself because you don’t need to find comfort in re-processing anything or talking to your ex. Be sure to perform self-care by eating well, sleeping enough, staying active and being connected to friends and family. It is important to give yourself and your ex space from each other; even if you plan to reconnect and talk in the future, initially, it is best to get that space to grieve. I would advise against jumping right into anything with anyone else.


"It’s been months but a lot of things remind me of them, how do I work past that?"

It is normal and natural to continue to be reminded of your ex after months, a lot will trigger memories especially if you had been together for a long time. Try to remove anything that isn’t necessary (a gift, decoration, etc) if it’s there by choice. If it is something that is part of your day or not able to be replace, try to create new memories with whatever it is. Engage in events and activities with a friend, try to change things in slight ways that can alter your experience (if it is walking down a certain street, try listening to a podcast or music that is completely unrelated to your ex while doing so). Some things can be altered, others can’t, and while it is important to recognize and feel the sad feelings when they occur, find ways to reframe and associate something new and positive with the things that remind you of them.


"I heard he has moved on. Why does it hurt so much and feel like I’m moving backwards?"

This sort of shock can definitely make us feel like we are spiraling. As if the person we lost is now “actually” gone because we have learned that they moved on.

It is best to maintain No Contact in the sense that you do your best to cut off any information about them. You don’t need to know about their new relationship nor do you need to see it - it won’t help your healing no matter how curious you may be.

Get the distance for yourself and keep it as cut off as you are able considering your circumstances.


"Is it possible to love someone deeply even if you can’t get along? How do you ever get over the pain of knowing that you deeply love someone but can’t stay for your own mental well-being?"

It is absolutely possible to love someone you can’t get along with- our emotional attachments tend to drive much deeper than some of our logic.

I would treat this as any grief honestly. Even if you had to end it for your emotional and mental well-being, the grief still looks and feels the same. It sounds like it was intense and even if not for a long time, it still impacted like you had a future and connection with this person. Don’t dismiss it for any of the details around the relationship and breakup, the feelings are the same and should be treated as any other healing.


"I would love to go no contact but he’s my direct boss. My office is within 8 feet of him. I’m his secretary. How do I do this? It’s only week one. Today I only spoke to him if necessary and only about work. Any other ideas? It’s awful. I’m heartbroken but need to try to move on."

This is absolutely a tough situation - especially with just the physical proximity. For starters definitely limit all contact to when you’re in the office and if you’re not in the office then keep it strictly to email so that you can control when you engage in it. I don’t know the relationship per say but it’s not completely out there to request that he texts less about work (if at all) and just sticks to email for your sake.

You’ve got the right idea to keep all communication strictly work-focused. No checking in outside of that for emotional comfort (for you or for him) - that can at least help with some emotional buffer. If you’re ever able to work from home, take advantage of that for sure. You’re really fresh into this but trying to take some control over how much exposure you have to him since you’ll need to have contact.



"It’s taken 5.5 months for me to feel grief of my ending things. Why is it delayed?"

It is actually extremely normal if you were the one to end things that your grief is delayed. Often the dumper’s initial reaction is to justify the breakup and feel relief about finally being done and single. 4-6 months is typical for when the grief then sets in for them. It’s after the reality of the loss sets it. Be kind to yourself and treat it as grief, feel your feelings and process then with others.

This isn’t exclusively for dumpers, of course, other times dumpees feel the same and have a delayed response.


"How do I handle being anxious/worried/annoyed that my ex will probably not wish me a happy birthday?"

Set your expectations that they won’t reach out and stay busy and occupied during the day.

I would suggest even going so far as to mute their texts or DMs so that if you do have the desire to see if they did reach out, you can be emotionally ready rather than a message catching you off guard. Then decide if you want to check - either at set times or only in the evening. You’ll be tempted I’m sure but set the expectation that they probably won’t reach out to help curb some of the disappointment.



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