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I'm a 34yo single mom of a 4yo little girl, and I started dating again earlier this year after 10 years. So I'm pretty rusty.

I met a really nice guy online, and we met IRL in June and have been dating since. He's met my daughter, and we've met his kids, and it's just been so wonderful to spend time together for Christmas this year. Naturally, we've become pretty serious.

He's insisted on paying at all of our dates so far. I've offered to split the bill and that I can afford it, etc, but he's insistent. He's always said that I'm a single mom and I can't be making that much and it's the least he can do.

The thing is, we have been doing more as a 'family' in December, and also looking at doing some more expensive stuff for Easter next year. He has kinda just assumed he'd be paying and it's making me feel uncomfortable. I'd really like to have a conversation about finances. I have said that I don't mind paying half and he's just not taken me that seriously, like "oh no don't worry, I can afford it".

We have discussed it before earlier on in the relationship, in a general way, and asked how I'm doing financially, and I've kinda waved it off and said "I make enough for what we need" because I was uncomfortable talking about it earlier on (it was date 3 or something). The truth is I am actually really financially well off and I wasn't comfortable talking about it so early on. I'm a professional engineer working online and we live in South Africa, where the cost of living is quite cheap, and I earn US dollars. So the exchange rate is really good. I make a lot more than I would locally. Probably 4 or 5x. I'm pretty sure I make more than he does.

Anyway, I didn't really want to talk about it back then, but now we're serious and it's been a couple of months and I am worried about him wanting to pay for all this expensive stuff when I really should be paying for our half.

I'm also concerned that he will have an issue with me making more than he does. It's a deal breaker if he wants me to stop working/not work.

How do I go about bringing this up without making a big deal about it?

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    Have you started making plans to move in together (with or without getting married) and amalgamate your families? Or even to have more children together? The finance discussion goes along with those discussions.
    – Dawood ibn Kareem
    Commented Dec 18, 2022 at 22:49
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    There seem to be a few different issues. If you can't tell him: "I'll pay for this" or "I'll split this with you" after dating a few months, that seems problematic. If you're worried about scaring him off with your wealth or insistence on paying your own way, then you need to talk about it ASAP, but that's really a separate question. There's also the question of what he expects in return for paying.
    – Stuart F
    Commented Jan 12, 2023 at 15:53
  • I’d try to find out what his financial situation is like. What is the right thing to do very much depends on that.
    – gnasher729
    Commented Mar 11 at 0:11

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I've had, on several occasions (vacations, family gathering with hotels and food, travel), this kind of situation to deal with. With friends, family, and SO.

With friends and family, it was quite easy, because you're more open to discuss this matter and the organisation needed. And do it long before the event, so you can adjust accordingly.

It was a little more tricky with a former SO, as, at the beginning of a relationship, you're quite shy talking about money. So, if you guys are going to be a family, you should start acting as one, and see if it works. That means: share, and everyone does its share. Like for chores, driving kids to school/sports, shopping...

Multiple options exists, we've used them after we discussed and agreed, everyone giving its preferences. The two best we've agreed upon and used were:

  1. You put an equal amount of money in a common pot, and use it to pay for the expenses during the holidays.
  2. You fairly divide the total cost of the vacation and decide who will pay what, so that, at the end, everyone has roughly spent the same amount.

It's a little bit of time and organisation, but it makes things run more smoothly.

What could be more difficult would be to raise the topic without upseting you boyfriend. Like many other sensitive topics, I just bring them with a light-hearted approach. Kind of:

Hey sweetie, about the holidays, I was wondering... How do we do X? What about Z?

Don't bring all the topics at once, just 2 or 3 important ones. And no money talk to start with, it'll come during the discussion. Once you decide on what to do, how and when, then, finally, the money. From there, you can raise your preferences, and say that you can take care of this and that, and ask if he's ok with that. The important thing is to just bring the topic, but not make it the important topic. Just a part of the discussion, a detail. Important detail, but just a detail.

Never had a problem doing that, because it was not pushy, not stubborn, just sharing points of view.

If he insists on doing everything on his own, then it's another story, and you'll have more to think about and discuss with him I believe...

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