I’m driving myself mad with my insecurities

[GenericUsername404]

I’ve been seeing a man for nearly a year now. I really, really like him, we always have an amazing time together, sex is great and I’d really like us to have a future together. But I’m really struggling to understand why he wants to be with me and I’m almost at the point of thinking I have to end it as I’m spending so much time obsessing over it.

Basically he’s absolutely gorgeous. I’m not saying that just because I fancy him, he is just an incredibly attractive man. Whenever we’re out together I see so many people, both men and women give him a double take as he is just one of those people who is so good looking that people seem to think he’s famous or something. Then inevitably I feel their eyes slide to me and I just know they’re wondering why we’re together. I don’t think I’m unattractive. I’ve never been particularly insecure about my looks before. I’m mid 30’s, not overweight, I make an effort with how I look and dress but I’m very much an average looking mum. I’m not saying this fishing for compliments at all, just I know what I look like, it’s fine but I’m not beautiful or particularly pretty, just a bit plain.

On top of this I’ve tracked down his ex girlfriend and his ex wife on SM (I know, I know) and they are both drop dead gorgeous and based on their jobs clearly very well educated and successful. I don’t have a degree, haven’t gone back to my customer services job since having DC and am a recovering drug addict.

I just feel that he’s so out of my league and I’m trying so hard not to develop strong feelings for him as I’ve had a pretty rough couple of years and really need to just protect myself from getting hurt for the sake of myself and my dc. He told me that he loved me a few weeks ago and I just couldn’t bring myself to say it back. I just mumbled something about him not having to say that he felt like that which (understandably) caused him to look really hurt.

I don’t know how to get over this or whether I should even try. I’ve never been in a relationship before where I’ve felt such a disparity.

But I know how much he earns and there’s simply no way that he could afford to do all the things he suggests we do if I let him pay all the time.

I don't like this. Red flag. He should not be suggesting things he can't afford.

I'd step right back from paying for things. Next time he suggests one, say, 'oh, can you afford that?' I've paid the last few times we've gone away and it feels a bit unfair. Can you come up with any cheaper alternative?' And see what he says.

Those hotel prices are ridiculous. If he's tight for money why would he suggest them?? You can get a perfectly nice hotel for a fraction of that. You need to start talking to him about money, op!

thefoundations flights came to less than £200. I paid nearly £3k for hotel.

thelastgoldeneagle the thing is if it were up to me I would have probably chosen that hotel anyway. It just irked me slightly that he suggested it when there’s no way he could have afforded it.

thelastgoldeneagle he’s not really tight for money, he earns a decent enough wage and owns his house. Just not enough to spunk £3k on a hotel when we could have easily got one for a quarter of that price. But then I never said “that looks nice, but why don’t we go for a cheaper one” or anything like that. I’m pretty sure he’d have been fine if I had suggested that though. I think. Oh God, I don’t know 🤦‍♀️

@GenericUsername404

thefoundations flights came to less than £200. I paid nearly £3k for hotel.

Can you not see what he's done here? He's got you to agree to paying for the hotel, and then after you've agreed to it, chosen an enormously expensive one.

He's manipulated £3k out of you, and you've let him.

I think the most salient question is: What stopped you from saying no?

I’m pretty sure he’d have been fine if I had suggested that though. I think

What are the other ways you think he might respond, if he hadn't been 'fine'?

thefoundations I hadn’t had a holiday in ages and really fancied just staying in a posh hotel tbh. It was only later that I started worrying that he’d suggested it when he couldn’t afford it.

I’m 99% sure he’d have been absolutely fine. Whenever we’ve had disagreements in the past or I’ve not wanted to do something that he has there hasn’t been an issue at all.

Yes the flights/hotel example is really cheeky. He’s taking the piss, but you’re letting him. Just start suggesting 50/50 split on everything, and see if he sticks around. Then if he does you can relax and stop stressing.

You could have just said “that looks really nice, but it’s a lot more than then flights. If we split the whole holiday 50/50 I can afford it.”

I’m 99% sure he’d have been absolutely fine. Whenever we’ve had disagreements in the past or I’ve not wanted to do something that he has there hasn’t been an issue at all

Yes, but in the 1% chance that he might not have been fine, how would you envisage that manifesting itself? The reason I'm asking is because there's some reason you agreed to his manipulation. There's a reason you didn't say to him, when you realised, that there was a huge imbalance in what you were paying for. There's a reason you haven't said to him afterwards 'How come I ended up paying for the lion's share of that holiday, when you were the one who suggested a £3k hotel?'

Something is making you uncomfortable about talking straight to him. What is it?

thefoundations I genuinely don’t know why I didn’t say anything.

How does he know that you have a large chunk of money? How long into the relationship did this come up?

Perhaps you could say to him that you are putting most of the money into a trust fund for your children so won't be able to splash out in future, and see how he reacts.

It does seem a bit like he sees you as a bit of a meal ticket, sorry OP. The phrase 'too good to be true' comes to mind. I don't mean that as an insult or anything, I'm sure you are lovely...but your spidey senses must have been tingling to write the OP, and it does sound like at the very least he is taking advantage.

Just step back from paying for things, or tell him you would like to go halves on things in future and see how he reacts.

What would you do if the same situation arose again, OP?

How long has the suggesting expensive activities etc thing been going on? Since before or after he knew you’d got a fair whack in your divorce? I’m just struggling to understand how he knows it’s fine to suggest such expensive things?

Initially I thought you were just being a bit insecure and hard on yourself, bit this money issue is .... There:s something not right there.

You both go on holiday, agree he pays for flights and you pay for accommodation .. he pays reasonably priced flights, but he suggests very expensive hotels and lets you pay for them. You paid proportionally how much more?! And he's not dumb, he works, has a house, pays bills, knows the value of money; it's v strange behaviour towards a single mum who.actualky earns less than him (if that's right?)

Since before or after he knew you’d got a fair whack in your divorce?

I missed that.

Does he think/know you got a settlement?

That should obviously be going towards yourself and your kids current and future security. It's not for him to commandeer on 500/600 quid a night hotels.

Do you own your property like him?

If my maths isn't dodgy, he paid 6.6% of the costs of your hol and you paid 93.4% (I don't know who paid for non hotel food, drink etc)

So basically you're paying him for sex? He's a gigolo

That's taking 200 for flights - you said it was actually less than that.

mulletsaremisunderstood that’s what I keep thinking and then I feel like crap thinking that maybe I’m being too hard on myself for thinking he wouldn’t want to be with me for just myself. But, yeah, writing it down does make it sound like money is more of a thing for him than I’ve previously thought about.

Wrt how it came up, it didn’t really. I know this is going to make me sound like a complete prick but it’s pretty obvious from my house that I’ve got a fair bit of money. I’ve been talking about selling off a few of the buildings in the grounds since fairly early on as he works in that sort of area and has been quite useful helping me out with the legal side of things.

marshmallowara I don’t actually work at the moment other than a couple of days in a charity shop. I guess that, combined with me having been given a bastard great house in my divorce that I don’t know what to do with makes him aware I’ve got money.

Cant believe you were mug enough to pay 3k for a hotel stay when he paid less than 200 quid for the flights...more fool you!

It doesn’t make you sound like a prick! And everything up until this money thing did sound like you were being insecure. I just think it’s a bit eyebrow raising for anyone to suggest such expensive things if they are hot the one paying for it. But maybe he thinks you’re totally loaded and that it’s a similar amount for you to pay x amount for a hotel as is it for him to pay x amount for the flights. Very hard to tell tbh but it doesn’t sit right with me.

You don't sound like a prick.

It sounds like he thinks from your house/buildings and it doing charity work that you're a well off yummy mummy who's made good in a divorce and can afford to splash cash on v expensive hotels .... It's a bit exploitative/avaristic tbh.

@Kittykat93

Cant believe you were mug enough to pay 3k for a hotel stay when he paid less than 200 quid for the flights...more fool you!

Did you not read he's spectacularly good looking and good in bed?

Only joking.

Mostly joking.