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I broke up with my boyfriend because he wasn’t transparent about his past, it hurts me and he doesn’t care. I told him in the beginning of our relationship that it was a deal breaker for me what do I do?

Last Updated: 19.06.2025 13:24

I broke up with my boyfriend because he wasn’t transparent about his past, it hurts me and he doesn’t care. I told him in the beginning of our relationship that it was a deal breaker for me what do I do?

1 — You have a keeper of guy who has a bad or checkered past, but he’s repented, and he’s working hard to turn over a new leaf — but he’s still too ashamed of his past to talk about it. . Give him some time, patience, and a very friendly and sympathetic ear.

Can you do this:

a) . Figure out what kind of people his current best friends are, figure out the kind of company he keeps (currently), and make the call on that basis.

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I need more information — Can you paint a larger, more detailed picture in the comment box below?

Here is what this one may boil down to — pick one:

Would you want his best friends, and the people he hangs out with, as your next door neighbors for the rest of your life?

I caught my husband of 20 years looking at inappropriate pics of women on TikTok or Instagram. I'm not sure., but when I told him he got mad and made excuses of why they popped up. I then told him how I've snuck on his phone and saw what he's been looking at . We had a horrible big fight. I asked him why did he even marry me when I see the type he likes . Nothing like me, I'm petite, blonde and blue eyes. These women are dark haired dark eyed and have curvy bodies, large breasts, etc. I just don't feel the same about him after this. I can't get over this

2 — You have a bad apple who not only has a bad or checkered past, but he hasn’t fundamentally changed, he’s the same bad apple he always was, and doesn’t want you to figure that out. . Leave him and don’t think twice.

— Please feel free to respond with follow-up questions in the comment box immediately below, thanks.

b) . How does he treat other people of lower status than him? . . . How does he treat the persons he doesn’t yet know very well? . . . How does he treat the check-out clerks, the gas station attendants, the bums and homeless people on the streets? . . . How does he treat stray dogs and cats? . . . Will he go out of his way to help someone he doesn’t know? . . . Is he quick to anger and curse, or slow to do so? . . . Can he hold a job for months & years without upsetting his co-workers or bosses or clientele? . . . Does he pay his bills on time? . . . Does he run up credit card debt and have bill collectors after him? . . . What does your mother and sisters think of him? . . . Does he have good manners on the phone? . . . Other than his past (before he met you), is he easy-going and easy-to-talk-to about everything else? . . . If he ran a business, would you recommend your best friends to do business with him? . . . Does he have some emergency savings? . . . Does he mow his yard, wash his car, go to the dentist as needed, and take his pets to the vet as needed? . . . Does he spend too much money on beer, alcohol, weed, lottery tickets, sports betting, cigarettes, porn, or other junk?

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