It’s never easy to let go of a relationship; learning how to go from lovers to ex-lovers can cause a lot of anxiety. Whether they’re sending mixed messages or you’re struggling with your own lingering feelings, learning how to deal with an ex can be difficult.

At least 90% of the advice letters I get have to do with breakups and/or an ex. Today, I’ll be answering a few of them.

If you’re new to the blog, Dear Dating Bitch is my advice column segment. I’m always happy to answer questions from readers, so if you’re in need of some advice, you can submit your questions here. And don’t worry – it’s always anonymous.

Now then, let’s get to the questions for today!

Help! How do I deal with an ex who's confusing me!
*Note: Questions may be edited for length/clarity

Dear Dating B: Some Advice on How to Deal with an Ex

Q: My ex-boyfriend says that he loves and cares about me, still. He also tells me that he wants us to be friends, but he never actually reaches out or contacts me first. What’s happening here?

Friendly-ish Ex

Dear Friendly-ish:

There are times in life when a question can only be answered by someone unwilling (or unable) to do so. Unfortunately, this is one of those times.

The only person who can give any sort of definitive answer on this is your ex. Everything else is pure speculation. Your ex may actuallylove, care for, and even miss you at times. He could also feel like he needs to keep some distance from you. Both of those things can be true simultaneously. You can love someone and still feel like keeping them in your life isn’t wise.

Maybe he’s fine with a friendship, but thinks that you need to be the one reaching out. If he broke up with you, for example, he may think that he needs to be respectful of your boundaries and let you set the tone going forward.

Or, maybe he doesn’t want to a friendship and just says so to avoid being rude. He could be doing the whole, “Sure, we should get coffee sometime,” thing that people do when they have no intention of ever getting said coffee.

But, again, the only person who can tell you for sure is your ex. If you genuinely think that a friendship is worth pursuing (and in your best interest), ask him. You don’t have to be confrontational or aggressive. Just state your feelings and confusion very clearly:

“Don, I appreciate that you’ve said you want to stay friends, but I’ve noticed you never initiate contact first. Is there a reason? I’d hate to push a friendship on you that you’re not actually comfortable with.”

Q: My ex-boyfriend blocked me everywhere—on social media and on the phone. I didn’t leave him alone (for specific reasons!) and then he changed his number. Will he ever come back?

Waiting to be Unblocked

Dear Waiting:

I highly doubt it. Blocking someone—whether that’s on social media or not—is a pretty clear boundary. One that says, quite loudly, “I’m not interested in talking to you.”

Your ex set a boundary and made that boundary known. Instead of respecting that, you continued to call him and pursue conversation. You mention that you had “specific reasons” for doing this, but without knowing said reasons, I can’t weigh in on whether or not they were valid.

Regardless, you did, in fact, ignore his clearly defined boundaries and his reaction was to change his number. Once again, I’d say hes sending you a pretty clear message; he doesn’t want to talk to you. I’m not trying to be harsh; I’ve been on your side of the street before, too. I fully understand the anguish of thinking “if only I could talk to him one more time, then I’d be able to change his mind.” But continuing down this road isn’t going to be helpful to anyone.

If there is a legal issue that needs to be resolved, contact a lawyer and have them do all the contacting from now on. Otherwise, let this guy, and any notion of him coming back, go.

Related Read: Why It’s So Important to Follow “No Contact” After a Breakup

Q: My boyfriend has broken up with me six times. Every time, he comes back. We’re back “on” right now but I know he’ll do this again. We’ve been together for 3 years and we really do love each other. Is this fixable?

On-Again, Off-Again

Dear On Again, Off Again:

Yes, but probably not in the way you’re hoping.

You and your on-right-now boyfriend are stuck in this cyclical pattern. This type of yo-yo relationship may be common, but it’s far from healthy. When a relationship ends, it’s usually because there’s a problem. A relationship that continuously ends, even when that ending isn’t permanent, suggests that the issues are deeper and possibly irreparable. And the constant uncertainty of how long the on period will last this time is clearly causing you some distress.

I’m sure you can see where I’m going here. The solution, my dear, is to end the cycle completely. That means being “off” for good. If I were you, I wouldn’t wait to see if (or, more realistically, when) he ends the relationship this time. Rip the Band-Aid off yourself. Otherwise, you’ll be setting yourself up for a never-ending cycle of anxiety and heartache.

Q: My ex wrote me an apology letter recently. I’m not sure how to handle this. Should I respond?

Letter from an Ex

Dear Letter from an Ex:

Do you want to? Are you interested in reconnecting with him, either as a friend or something more? Is replying to this letter going to benefit you in any way?

Unless you can answer ‘Yes’ to all of the above, then there’s no need to respond. It’s nice when someone who’s wronged you comes back to apologize later, but that doesn’t mean you need to forgive them.

Q: My ex recently added me on social media. We were “friends” there for a couple of months, but now she’s unfriended me again. Completely out of nowhere. Why would she do this?


Dear Ex-Friended

A new boyfriend who doesn’t like that she’s Facebook friends with an ex? Unflattering posts about her “last relationship” that she doesn’t want you to see? A sudden desire to only have IRL friends on social media? Your guess is honestly as good as mine.

Whatever the reason, she’s essentially telling you that she doesn’t want you in her life right now. Take that for what it is and move on with your day. And if she comes back later on with a friend request, feel free to ignore it.

☆ ☆ ☆


Learning how to deal with an ex without causing yourself additional stress is something few people can manage well. No matter what you feel in the moment, it’s best to take a few deep breaths and sit on the situation before reacting.

What’s your best advice for how to deal with an ex? Let me know in the comments below!

And of course, thanks for reading. If you’ve got questions of your own, make sure to send them to me here!


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  1. avatar

    I always find your answers in therlse posts really insightful and helpful. I can understand why it is difficult to deal with your ex and the advice you provide is to the point!

    1. avatar

      Thanks so much – glad you enjoyed!

  2. avatar

    This is a really helpful post for people who need help and advice when dealing with exs. Thank you for sharing.


    1. avatar

      Thanks for reading! Glad you enjoyed

  3. avatar

    This is just my opinion, but the boyfriend from the first letter sounds like he’s trying to turn you into a backup girlfriend. Be careful not to get strung along

    1. avatar

      That’s definitely a good point; it’s certainly possible. It’s always a good idea to take time before trying to have a friendship with an ex.

  4. avatar

    This is honestly such great advice! It can definitely be tough dealing with exes, but I think making yourself the priority and only doing what will benefit you is super important. Thank you so much for sharing x

    1. avatar

      I completely agree – thinking of other people is an excellent trait, but in terms of heartbreak, we have to be a little bit selfish sometimes.

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30ish Lifestyle blogger, relationship "expert," and modern-day agony aunt.
Sometimes humorous, always honest.