Should I Break Up With My Boyfriend? We Have Advice

should I break up with my boyfriend

By Jackie Pilossoph, Founder, Divorced Girl Smiling, the place to find trusted, vetted divorce professionals, a podcast, website and mobile app.

Are you wondering and asking your friends, “Should I break up with my boyfriend?” If you are even asking, the answer is probably yes. But you already knew that. Otherwise, you wouldn’t be seeking advice. Still, I’d love to help you figure it out.

Should I break up with my boyfriend? Let’s start by recognizing that dating after divorce is a little bit different than dating before marriage. It is the same in regards to the fact that men and women are out there on dating websites, meeting people, getting set up, and going on dates. But, there are lots of differences. Divorced people might date for different reasons than a person who has never been married, like for companionship or fun. There is one really BIG difference: Now, you’re not only searching for love, but as a divorced person, you’re not going to settle, right?


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Online Dating Coach and Stylist


That means that you realize you deserve only the best fit. I’m not taking about perfection. That’s impossible. But rather you might put a little more thought into things than you did as a young, single, person with such little life experience. And I can say, as a divorced person, if you don’t, then you should!

So, how do you know if you should break up with your boyfriend, or if this guy is really a good guy for you?

Every situation is different, and only YOU know what’s in your heart, but here are some no-brainers when it comes to: Should I break up with my boyfriend:

Here are some scenarios and my advice on whether to love him or dump him.


1.He’s pressuring you into marriage after 3 months of dating: dump him!
He tells you he wants to spend the rest of his life with you after a year of dating, and he doesn’t care in what capacity that is, whether it’s marriage, co-habitation or just dating forever. He loves you and he just wants to be with you. He’ll give you all the time you need. Love him!



1. He talks about his ex wife and uses the “b” word when referring to her: dump him!
While he may not have the best relationship with his ex, he respects the fact that she is the mother of his children and his main focus is on them, not her. He’s over it and doesn’t like her or hate her. His relationship with his ex is strictly all about the children. Love him!


1. You spend hours getting ready for your dates, you buy new outfits, get your nails done, get Botox, lose weight, and he doesn’t really compliment you or seem to notice: dump him!
You show up at his place in your sweats with no makeup. Your hair hasn’t even been brushed and you have zit cream in four spots on your face. He smiles and tells you how pretty you are:Love, love, love him!


1. His job isn’t going well and you are afraid you are going to have to support him for awhile and you are thinking you don’t want to do that: dump him! (not because he’s a bad guy, but because you don’t truly love him or you wouldn’t think twice.)
2. His job isn’t going well and you think to yourself, ‘If he lost his job and I had to support him for awhile, I’d be fine with that because we are like family, and I know he would do that for me.’ Love him! (because truly, you do.)


Cherie Morris, J.D. - Divorce Coach and
Founder, Dear Divorce Coach


1. When you have to get together with his family, it feels like an obligation, but you do it because you know it pleases him and that’s what a good girlfriend does. But you truly dont like or respect any of them. dump him!
You look forward to seeing his family. They feel like YOUR family. They arent perfect but they are good people who you are happy to bring your children around: Love him!


1. When he isn’t feeling well, you let him get his rest and you go out with your girlfriends. dump him! (let him find someone else who truly loves him because clearly, you don’t.)
2. When he gets sick (other than COVID), you go over there with chicken soup and Nyquil and Gatorade and you play with his hair. You don’t even care if you catch it. Love him!

1. You are constantly going out with other couples because it’s more fun and you want to party. dump him!

2. Even after months and months of dating, the two of you still look forward to Saturday night dinners by yourselves. You still sit and talk and flirt and your dates still feel like third dates. Love him!


1. You just can’t get used to sleeping in the same bed with him. He’s a covers hogger and he snores. dump him!
You’re loving the naked cuddle, even after years.Love him!


Bridging the Gap Between Conflict and Resolution


1. You have completely different political views and are constantly arguing about issues. You just don’t get his stance. He’s also mean and doesn’t respect your views. dump him!
You have completely different political views and are constantly having interesting debates and discussions. You respect his opinion and he respects yours.Love him!


1. You feel lucky that he loves you because he’s so gorgeous, professionally successful, and everyone loves him. dump him!
You feel lucky that you have each other, and you love the person YOU are with him. You love that he makes you a better person, and you love that he thinks the same about you. Love him!


1. When he gets home from the gym and you haven’t seen him all day, you tell him he needs a shower and wont touch him till he takes one. dump him!
When he gets home from the gym, and you haven’t seen him all day, you throw your arms around him and hug him and never let go, even if he stinks. Love him!


1. You’re having a hard time imagining him fitting into your life with your children and your family and your career. You tell yourself it will just work itself out. dump him!
You can’t imagine NOT having him in your life. It’s not even a factor that enters your mind. Love him!

In closing, these are black and white examples, and things that might get you to think about whether or not you should break up with your boyfriend. Every situation is unique, and you are the only person who can make this important decision. But I will say this. If you stay with someone and you continue to be unsure and you’re not breaking up because you are scared to be alone, or scared you will regret it, think again. The scary part is staying with someone and missing a chance at being with a person who makes you so much happier and is such a better fit.

Like this article? Check out “9 Signs of a Healthy Romantic Relationship”

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    Divorced Girl Smiling welcome video
    Jackie Pilossoph

    Editor-in-chief: Jackie Pilossoph

    Jackie Pilossoph is the Founder of Divorced Girl Smiling, the media company that connects people facing with divorce to trusted, vetted divorce professionals. Pilossoph is a former NBC affiliate television journalist and Chicago Tribune/Pioneer Press features reporter. Her syndicated column, Love Essentially was published in the Chicago Tribune/Pioneer Press and Tribune owned publications for 7 1/2 years. Pilossoph holds a Masters degree in journalism from Boston University. Learn more at:

    2 Responses to “Should I Break Up With My Boyfriend? We Have Advice”

    1. Jamie Beck

      I read this and had to smile at some of the comments. I’m still married…but I remember having some of those debates in my head back when I was still out there dating! Of course, if I literally complied with each and every one of these edicts now, I might have to ‘boot’ the hubby (which I don’t want to do)! I mean..he does hog the covers and snore! 😉

    2. Cadbury

      “You spend hours getting ready for your dates, you buy new outfits, get your nails done, get Botox, lose weight, and he doesn’t really compliment you or seem to notice: Boot him!”

      Boot him? Sorry, but I would have already booted her. I know that she’s trying to impress me, but I wouldn’t want to be around someone who has to spend hours getting ready for a date, wastes time on her nails (yes, getting dirt out from under the fingernails is nice, but I think nail polish is unattractive, as is makeup). Great outfits don’t impress me. Botox? Really? That’s difiguration.

      Losing weight might be nice and I probably would notice and mention that (I’d rather be around an athletic woman than a princess), but I’m seeing in this description of a superficial, artificial woman who wouldn’t be any fun to be around.

      I think that a lot of women think that this impresses a man. I think most men would rather have someone fun and relaxed, rather than someone who is this hung up on her appearance and would make me feel like I have to take her to a Presidential Inauguration or a $500 dinner at a 5-star restaurant to have any fun.

      I’d rather meet her in sweats. Or jeans.

      And please, perfume makes me want to gag.


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