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Is sending me money a red flag?

387 replies

Kenyaparks · 11/05/2025 08:52

So I’ve been talking to this man for about a month now. We’ve done loads of phone and video calls. He lives out of state but he happens to live in the state that I’m moving to in a couple months. He is also coming out to where I am to visit me before I move out there.

I jokingly asked him for coffee money and he sent me some, I told him jokingly that it wasn’t enough and he ended up sending me more money? It was all jokes I didn’t think he was going to obviously do it, I definitely appreciate it. I was in the store today and I told him he should by a watch from the store I was at? He asked me if I wanted it and that he would send me the money… I obviously declined the offer.

is it a red flag that he’s sending me money and hasn’t met me yet ?

OP posts:
CautiousLurker01 · 11/05/2025 10:55

Phunkychicken · 11/05/2025 08:58

You are absolutely the red flag seeing how far you can push him

Indeed. You need to send the money back with a ‘I really was just joking’ note.

Bestfootforward11 · 11/05/2025 10:55

I’m not sure why you keep asking for money. You said you ‘jokingly’ asked for money for a coffee and he sent it. You then made another ‘joke’ for more money which he sent. You ‘definitely appreciated it’. You need to stop this. You know exactly what you are doing and were trying to see how far you could push it. And now you are trying to justify this to yourself. I cannot imagine making ‘jokes’ to anyone about money (particularly someone I don’t even really know) and then accepting money sent. Send the money back and stop communicating with this man. You are getting yourself into a situation with someone that you don’t really know and engaging in behaviour that is creating obligations. Is he a red flag? The behaviour you later describe does not sound healthy. But neither does yours. You have agency here and need to step back and reflect on your own behaviour that is also not healthy and leading to potentially unsafe situations.

FiveShelties · 11/05/2025 10:54

Kenyaparks · 11/05/2025 10:40

We were on the phone and I had to take a phone call and I told him I would call him right back. He told me not to hang up. I did and ended up calling him back told him that my mom was just calling to ask me if I wanted something to eat… he then replied saying “couldn’t you have just texted her that” …. At that point I hung up on him, I found that very disrespectful.

But you don't feel it is disrespectful to ask for money?

Yuck.

Lovingthehamsterwheel · 11/05/2025 10:51

Op you sound like you are very naive, leave this man well alone.
Yes red flag completely, he could be love bombing you, scamming you, gaining trust and finding out your details. Sending small amounts of money then one day hes like, oh send me your bank details for a large cash deposit, finding out your apartment number etc

londongirl12 · 11/05/2025 10:51

Kenyaparks · 11/05/2025 10:40

We were on the phone and I had to take a phone call and I told him I would call him right back. He told me not to hang up. I did and ended up calling him back told him that my mom was just calling to ask me if I wanted something to eat… he then replied saying “couldn’t you have just texted her that” …. At that point I hung up on him, I found that very disrespectful.

So your opening post was about money, then there’s all these extra things that scream red flag. By asking him for money you’re playing this weird game with him. Just stop talking to him for goodness sake.

Dangermoo · 11/05/2025 10:50

Sounds like you're testing the waters as to how much he's willing to splash the cash. Now you're turning it round on him to look for ulterior motives. Quit the silly game playing.

TryingToBeHelpful267 · 11/05/2025 10:48

Asking for money is a red flag. Him paying it makes him foolish but also means he probably thinks you owe him.

Dangermoo · 11/05/2025 10:46

Namechangeforthis88 · 11/05/2025 08:55

The red flag is you keep asking for money.

😅😅

bramblefoot · 11/05/2025 10:46

So you hinted you want some money from him, were happy to give him your details, and accepted the cash -Why? I can't imagine even jokingly asking another adult I've just met for money, or saying it's not enough knowing they obviously are likely to send more, that isn't normal OP and you clearly did want money from him or it wouldn't be in your bank account in the first place. If I started dating someone and they 'jokingly' asked for money I would block them.

24 is an adult age, stop asking strange men for money and accepting it, stop talking to him and cease contact (block him) if his behaviour now is making you uncomfortable or you feel unsafe.

gerul · 11/05/2025 10:45

So OP sent the money back but then keeps "joking" that she wants more money. OK. Then followed by a load of dripfeeds about how awful he is.

MereNoelle · 11/05/2025 10:42

Kenyaparks · 11/05/2025 10:40

We were on the phone and I had to take a phone call and I told him I would call him right back. He told me not to hang up. I did and ended up calling him back told him that my mom was just calling to ask me if I wanted something to eat… he then replied saying “couldn’t you have just texted her that” …. At that point I hung up on him, I found that very disrespectful.

Ditch him then? Not sure what you’re expecting people to say? ‘He sounds like a keeper, go for it’?

Kenyaparks · 11/05/2025 10:40

We were on the phone and I had to take a phone call and I told him I would call him right back. He told me not to hang up. I did and ended up calling him back told him that my mom was just calling to ask me if I wanted something to eat… he then replied saying “couldn’t you have just texted her that” …. At that point I hung up on him, I found that very disrespectful.

OP posts:
EdithBond · 11/05/2025 10:39

You shouldn’t expect, allow or ask for him to pay for anything for you, even as a joke. You’re an independent adult. Pay your own way. Sure, you can take it in turns to pay for coffee, dinner, buy each other little gifts. But it shouldn‘t be one-sided.

By joking about him paying, you’re indicating to him you want an unequal relationship, where he pays for things for you. Unequal relationships can be unhealthy.

Him sending you money is a red flag. It’s transactional. He’s either trying to get you into a position where you owe him and he should expect something in return. Or he’s so desperate for a relationship with you or has such low self esteem, he’s willing to pay. It’s possible he believes it’s ’gentlemanly’, but that suggests he believes in old-fashioned gender roles, which also isn’t great. An enlightened man would expect you to pay for yourself, with your own money.

If he keeps paying money into your account, make it clear you don’t want it and, if he keeps doing it, you’ll have to consider ending the relationship. Don’t joke about it anymore. Apologise that you did.

Pressuring you to give him your address is a serious red flag. A decent man wouldn’t do this. He’d understand it wouldn’t be sensible until you know him better IRL. Have you asked him why he wants to know it? Set clear boundaries and simply say you don’t want to share your address. His reaction will be telling.

It’s not a good idea to give a man you solely/mainly know from being online (including video calls) your address or invite him to your home. Or go to his home for the night without having met him a good few times in person. People can heavily curate themselves online, including in video calls. Being with someone IRL you see spontaneous reactions in public, how they treat others etc. And instinct (bad vibes emanating) works better.

Don’t go to his home to stay the night without visiting a few times in the day and figuring out if it’s safe, e.g. could you get out if you wanted/needed, are there neighbouring homes, how easy could you get home/into town if you left? Get to know him in person first, meet his friends, work colleagues and ideally family.

If you want to have a romantic night, stay in an hotel with professional staff. And tell a trusted friend the name of the hotel and room number and give them his phone number. Let them know you’ll call them at a particular time the next day to let them know you’re OK. If they don’t hear from you, they should call you and (if no answer) then call the hotel and ask them to get a message to you. Basic safety measures that aren’t OTT.

If he already knows your address, or finds out, make sure you have safety measures: friendly, trustworthy neighbours who keep an eye out for you, friends nearby who you could text a code word to if he turns up and acts weird, spy hole, good locks etc.

MatriarchCaz · 11/05/2025 10:39

Namechangeforthis88 · 11/05/2025 08:55

The red flag is you keep asking for money.

This.

Cardinalita90 · 11/05/2025 10:38

You clearly know something's off with this guy from all your follow-up posts so just cut contact. DO NOT give your address. Womens intuition is there for a reason.

However, it's very unclassy to keep making jokes about needing money from him (or anyone else). Don't do that again.

Dunnowotot · 11/05/2025 10:37

@Kenyaparks You are the red flag 🚩🚩🚩

TheBroonOneAndTheWhiteOne · 11/05/2025 10:37

It all sounds dysfunctional.

It's very worrying that he wanted to know who you were texting. I mean you've only been chatting to this man for four weeks FFS. You could be sending a message to a family member. It's none of his business.

GRex · 11/05/2025 10:35

Kenyaparks · 11/05/2025 09:50

We’ve only talked for 4 weeks … He shouldn’t want to know my exact apartment…

Sigh. Drip drip drip.

You're 24, why do you think you need permission to stop talking with someone who makes you uncomfortable? Just stop contact. And stop asking men for money, it isn't cute it's weird.

BunnyLake · 11/05/2025 10:27

Just step away, you may be weird for asking for money but he sounds potentially dangerous.

Nanny0gg · 11/05/2025 10:26

Kenyaparks · 11/05/2025 09:50

We’ve only talked for 4 weeks … He shouldn’t want to know my exact apartment…

And you shouldn't be asking for money

(I fail to see the 'joke')

RareGoalsVerge · 11/05/2025 10:26

Why did you ask him for money/the watch etc? What a weird way to interact. Probably best to call off this particular relationship because it's got off to such a dysfunctional start that it can't now go well in the long term. Maybe get some counselling to work out how you want to actually interact with a future partner and start again when you have worked out why you did such a thing.

Hwi · 11/05/2025 10:26

Your behaviour is a red flag.

Catsandcannedbeans · 11/05/2025 10:25

I mean I don’t think it’s necessarily a red flag in itself. When I first started dating DP if I was chatting to him and I was in town he would send me money and say grab a sweet treat. He still does. Or if I was out after work and he wasn’t there he’d send me food or a drink. The difference is I never asked him for money and I had met him (we met at work). I asked him why he did it and he just said because it made me so happy for a few quid it was a no brainer. It is nice to know someone is thinking of you I guess.

This can be a fetish for some men tho. It’s called financial domination. If he’s into that he will probably be into some other strange things (feet is a big one). I speak from experience here as I did once go out with one of these men… it’s not really worth it. At first it was great and I got an iPhone and a bunch of other stuff I would not have been able to have at the time, but there’s a more insidious side to it. He was also super controlling.

From reading your updates, this man sounds insane. Do not go and stay with him. The money thing alone is not a red flag… everything else is. It’s very full on for 4 weeks especially if you’ve never met. I’m all for a whirl wind romance but this sounds like the start of an episode of Criminal Minds.

Gruttenberg · 11/05/2025 10:25

He sounds like a pay pig and you sound like an online sex worker. Just own it and be honest.

LittleMonks11 · 11/05/2025 10:23

And block this man - none of this sounds right