Should I go back to him?

He’s 19, I’m 34. We broke up after only a month of dating because I found out some things about him which made me lose trust in him. I found out that he used to sleep with older women for money, and that he was planning to ask me for money too, but he said he fell for me and decided against it. However, he did ask for my help eventually in paying off some gambling debts, and it became the reason we broke up.

I really have strong feelings for the guy and was very depressed. He made me question my worthiness of being loved. During the week we were broken up, I started sleeping with other guys I used to sleep with before meeting him. I wasn’t horny – just needing validation.

Last night he reached out to me wanting to see me again today. I agreed because I really missed him. I don’t have a plan – I know he will try to get back together. And I know I will agree. However last night he asked me via text if I’ve had sex with anyone else while we were apart, and I lied and said no. I know that that’s the deal breaker and he’s not going to want me back when he finds out that I did.

Should I take him back in the first place? I’m willing to trust him and forget about the past, just to have him again in my life.

Should I tell him the truth? It will probably mean the end of everything for good. There’s a chance that he will eventually find out that I slept with other men while we were apart. I’m willing to take that chance.

I love him and want to be with him no matter how stupid it sounds. I’m hoping that someone with experience on this matter can offer some insights to help clear my head. I am meeting him in a couple of hours.

Category: Dating & Relationships asked July 20, 2014

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Lonely

5 Answers

First, has he done anything to regain the trust you said he lost? Second, if you were broken up, do you think it should matter whether or not you were sleeping with anyone? I couldn't say for certain, given what we know, but that could be a way to manipulate and control you. You have no obligation to discuss what happened when you were broken up, but you really should consider whether any of the factors that broke you up have changed. I know younger people can be really hot, and there might be a fear that you won't get to be with someone that young or hot again, but you did break up for a reason.

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damaged

625

I understand that it's not fair to judge someone on their past. But it sounds like his past is coming back to haunt him. Prostitution? Gambling debts? Who's to say he's not just using you? Especially if he's asking for your money. Old habits are hard to break... so is he ready to give up gambling what he doesn't have and asking for money for sex? Age is just a number, yes. But you must be so much more mature than he is. Is he seriously ready to be in a committed relationship with someone like you? And don't most men fully mature in their mid-twenties? Which means his taste is likely to change. And honestly is always the best policy. Eventually, he'd find out that you slept with other people and when he does, it'll be much worse than if you were just straight about it. You have to ask yourself if he's the type of person you want to trust. You may not be able to judge him on his past, but his past at least shows you his habits and patterns. A month of dating may not necessarily be enough time for someone to change all of his ways. Really think about this, who he is, what he's done, and how he could help you. This sounds like a tricky situation that very well may end badly. I wish you all the best and hope you find a decision that makes you happy.

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Carrie

349

Absolutely not, ma'am.

You already asked this question to us, but this time you left out that he uses older women for their money to pay off gambling debts.

Do NOT stay with that young man. Send him on his way and do not continue to allow that young man to weasel his way into your assets.

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Humanist Hope

16,417

Whatever you do, don't lie and don't give him more money. He'll go away if the money is the only thing he wants.

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rinseandrep

7,397

Without going to your profile, I know this is the second time you've asked this. Have the answers changed to the point where people have given you the permission you want to see this loser? Honestly, if he makes you question things this much, that's your answer right there. You know he's toxic and has done absolutely nothing to regain your trust - don't let any issues you might have personally thrust you back with him because you don't want to be alone; you're better than that.

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thelovelymsdoe

195