Boyfriend wants me to put his car under my car insurance

Yep!

All of a sudden he can’t pay his car insurance or rent.

If OP says no then he’ll act like he can’t get to work or has no where to live.

No wonder he keeps trying to worm his way back in.

Life is too short. Run like the wind.

I despair at you!

Your self esteem must be on the floor to keep going back to this pathetic loser, broke and asking for handouts, yet simultaneously paying for expenses he can’t afford.

What’s wrong with you???
You have your own child to look after too??

Dump him.
Block him.
Never, ever go back to him. Don’t talk to him again. Don’t go back for another round of rebound sex (I can’t imagine what else has got you so hooked on this pond scum!)

much older than you think... thanks for the harsh honesty... I needed to hear it. I've ended the relationship several times because of my concerns but he always comes back and I haven't found anyone else who I like

This stood out to me. You haven't found anyone else who you like. That doesn't mean you have to put up with dross like this.
@CrossingBoundaries007 I presume you like and love your child. And you should like and love yourself.
And that like and love must come before anything else.
You don't have to "find anyone else who you like" because you have yourself and your child.
I know it's lovely to have a wonderful partner whom you like and love and likes and loves you back. But that doesn't mean you put up with any old crap just because you can't find anyone else.

Please concentrate on loving yourself. I'm absolutely sure you love your child and do wonderful things with them. But maybe you don't love and like yourself enough. Do wonderful things just for you. Love yourself. Spend time with yourself. Plan things just for you.
And then once you are happy in and with yourself you can move forward - that might be dating again (decent people only) or it might be saying hey, I love being single and having this great life I've created for myself so I don't want anyone else.

These hobosexual types make a beeline for people who haven't got the best self-esteem or maybe aren't secure in themselves for whatever reason. They know they can manipulate people like that.

OP, say NO to this car insurance thing. And absolutely NO to any hints about moving in with you - because that will be the next thing when he can't pay his rent. Oh, darling, it's just for a few weeks until I get back on my feet, the nasty landlord's kicking me out. And then he's in, feet under the table, in your and your child's home. You end up paying for everything. He then sinks into depression (he says) and can't work anymore. His business goes tits up. And he's too comfortable living at your expense to bother about looking for a job. Once you start making noises about him getting a job he'll squeal mental health at you to make you back off.
Textbook hobosexual behaviour.

I'd agree but people like him do seek out people they can utilise as a resource. In this case a financial resource. OP has been lending him money and doesn't see a problem with that because he paid it back, but that was just the softener so that if he asked in future fir her to take out a loan there's more chance she will think ok, well he paid it back before so why not. Or likewise with the insurance, because he paid her back before in his mind she's less likely to see it as a problem. Even if she refuses it was still worth asking.

I've known him for a couple of years and it was never this bad he's paid for all his bills without issues (including bent) but it's just recently that shits hit the fan

More likely it's "just recently", having put up with him for a couple of years and keeping on taking him back, that he's worked out you're good for ongoing requests

Give him his due though, he's inventive ... the loan request didn't work out and you haven't let him move in (so far) so he keeps thinking of something else

Then maybe it's time to think about why you keep taking him back. It sounds like you have your own issues. When you say you couldn't find anyone else you liked, what you are actually saying about yourself is that you think this is the best you can get, that you don't deserve any better. That's not healthy. Look into the Freedom Program, it could be the best £15 you ever spend. If you were stronger if yourself you would not be drawn to men like this. He isn't going to bring you future happiness because he's too financially tangled and another woman's life. You deserve better.

Bloody hell!

So he asks you to take a loan out for him, he asks you to put him on your car insurance, you’ve broken up multiple times and he’s at risk of completely losing his license and home - yet has a child in private school.

OP you are being taken for an absolute mug!!

Next thing he will be homeless and guilt trip you into letting him live at yours and then using your car.

You have to end this once and for all, before he moves himself in and you’re too nice to say no.

How can you be a single parent and afford your bills, yet this man can’t.
As a single parent, a partner should be helping you, not leaving you short of cash which could be spent on your on kids.

Its laughable that his kid is in private school and yet he’s using a single mother to help pay his bills.

Run for the bills OP.
This will only get worse.

Keep the relationship casual.
If anything, you could refuse to lend him anymore, say that he needs to sort out his finances and you could gift him a one off part payment of his yearly car insurance - never to be repeated - on the understanding that he will sort out his finances with his ex even if it means that the child needs to swap schools.
If the one chance fails, leave the relationship for good.

I'd put money on him not realising that, if I were ever inclined to gamble.

I've known many people like him. Well meaning and full of good intentions, but never think things through; impulsive. A dreamer.

Obviously he is someone who might seriously put the OP at risk, and she needs to not put herself on the line. It just doesn't sound deliberate or malicious, though.

run as fast as you can

He’s asked you to take out a loan and now car insurance fraudently. What next - pay the school fees, his rent? Will he find himself homeless and want to move in?

Don’t you want a relationship to ENHANCE your life rather than give you additional stress? I think you can do much better than this man. Life will be much less stressful without him in it if you ask me…

He sounds like a real Walter Mitty.

He is lying to you @CrossingBoundaries007
The more you post about him the more it doesn't add up. The loan request would be the final straw for me.

I'm not surprised he is divorced. His ex saw sense and kicked him out.

He’ll be banned from driving soon enough so I wouldn’t worry about his insurance. If he thinks it’s expensive now, wait until he tries to renew it after being disqualified. Ha ha! What a fucking loser. I wouldn’t touch a guy like this with a barge pole. He’ll be needing lifts to pick up his child from the posh private school that he can’t actually afford.

I would second all of the opinions here. I would politely explain to him that it doesn't sit right with you as it sounds as if it would be illegal. I'm not even sure how it would work....is he asking you to pay for his insurance and be the main driver yourself and add him as a named driver? If this is the case, as others have said, the insurance company would surely charge YOU a fortune because of his driving history? And this is not fair to you. Do you have your own car? If so, would this mean that you would be having to pay for two lots of insurance? And has he asked how long he would like you to do this for? I really don't think it's a good idea; just reading this has made me feel uncomfortable because you sound nice a really nice person and you don't want to be taken for a ride (if you'll pardon the pun). Even if he is well intentioned and loves you, he shouldn't be putting you in this awkward position. If it is illegal, he could be getting you into a lot of trouble. Please be careful!

You're deserve better than this OP,

I use to work in car insurance;what he's asking is called fronting and it's illegal.

It doesn't. Why isn't he paying maintenance for his children? And if he is then why is he also paying their full rent and school fees. Sounds like he's not telling OP the truth but she comes over so gullible it probably isn't difficult for him to bullshit her. None of this adds up. There's no way she wouldn't have been involved in the private schooling meetings.

I think from your updates, you're starting to wise up as to why you shouldn't agree to support his latest cheeky fucker request. Glad to hear you said 'no' to his request for a loan too...and in that respect and the reason why you've posted a question on here, it shows that your gut feeling was that you should also say no to the car insurance.

Question is, why do you think a 'no' to this latest request required an AIBU question on here? You felt strong enough to reject his loan request so why not the car insurance? Is he applying more and more pressure each time money/credit is asked for? Do you not feel that you have sufficient 'reason' to say no to him this time round(hence why you asked in your 2nd update)?

Always go with your gut feel OP. Given that he had previous debt before you met him, he's not going to miraculously change now so going forward you KNOW that you will always be bailing him out for something or other. And that's not fair, particularly when your hard earned money will be paying his ex-wife's rent, his kids private school etc whilst you and your child do without. You know what's coming if you stay with him OP so best get shot.

Id be running the moment I heard the words im divorced and 3 kids.
No thank you.

Run for the hills. Dont tie yourself to this careless, irresponsible feckless person or you’ll spend your struggling and purging from one crisis to the next. Dont get pregnant or you’re in for a life of misery.

I can’t highlight this post enough to you @CrossingBoundaries007 do not bail this guy out

his wife can get benefits and the private school thing can change.

NONE of this is on you to fix

You say that like you were actually asserting yourself but the fact you split with him multiple times and only got back with him because you couldn't find anyone else you liked is incredibly naive. Can you honestly not see what a terrible bet this man is to have in your child's life? Asking you to take out loans, asking you to committ insurance fraud, I mean with kindness are you really this desperate for a boyfriend?

In addition to all of the other reasons pp have already listed, If you took out an insurance policy for him, this is called Fronting and is illegal.
If the insurance company find out, any claim would be invalid, the policy would be cancelled and a marker placed on your name meaning your own insurance may also be invalid/cancelled and you would subsequently find it difficult to get car insurance in the future.
I would imagine the fact you had 2 insurance policies on 2 different cars that you were claiming were both your main car, would lead to Insurance Company to be suspicious of fronting in the event of a claim and to investigate. It would be you suffering the consequences for this man.
His story doesn't add up anyway - why would not paying his insurance mean he was unable to get a new policy? Surely he could just pay the year policy cost up front as is always an option? If he can afford £7000 x3 terms school fees , he can afford a (?) £500 year insurance policy.