How do I (mid 30s F) bring up finances in a new relationship without sounding transactional to BF (late 30s M)?

r/

TL;DR:

Been exclusive with BF for about a month. Both want a life partner. He makes ~2x my income and seems financially stable, but he’s cautious about money (often hesitant to pick up the tab), yet spends big on luxury items like sports cars and watches. I’m a single mom dealing with legal expenses and want to make sure we’re financially compatible long-term. How do I bring up the topic of money without sounding transactional or making things awkward this early on?

I (mid 30s) and my BF (turning 40) have been exclusive for about a month now (he suggested). We both share the same long-term goal—finding a life partner—and have already talked through most of the important topics for marriage, except finances.

We live in a high cost of living area. I’m a single mom to a young child, make about $120K (early in a new career I started after my divorce), and rent a home. A large portion of my income goes toward ongoing legal fees for custody issues (unfortunately).

My boyfriend is in mid-career and makes around $250K. He rents a house from his parents at market rate. He’s mentioned before that he doesn’t want a “gold digger,” and many of his stories about bad dates center around women expecting him to pay at restaurants when they weren’t actually interested in him. So I’ve picked up that he may be more frugal or sensitive about finances.

That said, last week he told me that he buys an expensive sports car every two years (he currently owns a really nice one) because he gets bored—and also enjoys collecting luxury watches. While I don’t think he’s in debt, I don’t really know.

So far, he pays for dinner when we go out (usually at my suggestion), but often seems a little hesitant—like he’s mentally calculating things or just not relaxed about it. I’ve dated people in the past, including my ex-husband, who didn’t stress about who paid and generally picked up the tab, especially if they were the higher earner. This hesitation is new for me and has made me feel a little unsure.

Finances are obviously a major part of long-term compatibility, and while I really like him and think he has great qualities as a potential partner (and eventually a stepfather), I want to make sure I feel comfortable before things get more serious. He’s even said he’d like to meet my child at some point, and I explained that I don’t introduce anyone unless it’s a very serious relationship—he was respectful of that.

So, my question is: how can I bring up the topic of finances in a thoughtful, non-judgmental way at this stage of our relationship? I don’t want to sound transactional, but I also don’t want to sweep this under the rug. Any advice would be appreciated.

Comments

  1. Summer_is_coming_1 Avatar

    I don’t understand what you want to talk about . He’s paying your dinners and am assuming you are not dating him for long as he hasn’t met your son . Usually you’d get to be exclusive after meeting your son . What if your son doesn’t like him or vice versa ? I don’t think you should ask him anything about his finances as you have become exclusive very recently and he still hasn’t even met your son ! I am not sure why’d it bother you for him having fancy cars or his frugality . It’s his money and you are still new in the relationship.

  2. EmykoEmyko Avatar

    What exactly are you trying to ascertain? Whether he’s truly solvent and financial responsible? Or the spending break down he expects within a relationship? Whether his lifestyle is within your means? It’s not clear from your post.

  3. mononokeprincesss Avatar

    You can be curious and ask him how he thinks about money (spending, investing, etc). Can share your views as well so it’s a discussion. But yeah treat it like an open conversation where you are learning about each other and your (financial) habits.