Dear Penny: My Dates Assume I’m Broke Because I’m a Single Stay-at-Home Mom

Two people look nervous on a first date.
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Dear Penny,

I’m a 30-year-old woman. Sixteen months ago, just a few weeks into the pandemic, I lost my husband. As a result, my two young children and I each started receiving monthly Social Security benefits. Our checks combined are enough that I was able to quit my job and become a stay-at-home-mom to my girls, ages 5 and almost 2. 

I also purchased a new, nicer home in a beautiful upper-middle-class neighborhood, and this is my only existing debt. I manage money well. My credit score is great. I have a security cushion, savings accounts for my kids, and even a special account for vacations and fun money. I will receive this money until my children turn 18, so I have some time to re-establish a career down the road. For all intents and purposes, I’m financially stable for the foreseeable future. 

I’m interested in dating again, and I’ve tried a little, but one of the first questions I’m asked by a potential partner is, “So, what do you do?” And when I respond that I’m a single, stay-at-home-mom, most men seem to assume that my life must be a dumpster fire. Or they immediately follow up with, “How do you stay afloat if you don’t work?” And then I’m forced to jump into saying I’m a widow perhaps sooner than I’d like, and it scares men off. Emotional baggage is scary, I get it…

What can I say to make myself sound as stable as I am? Is there a way to divert the “what do you do?” question without seeming like I’m withholding something sketchy? Or a way to make it sound better so men won’t turn and run for the hills? 


Single, Stable and Stereotyped 

Dear Single,

If only dating didn’t seem so much like a job hunt. Too often, it feels more like an exchange of resumes than getting to know a person.

Your letter is a good reminder about why we shouldn’t make assumptions about one another’s finances. There are plenty of people with good jobs whose finances truly are a dumpster fire because they spend beyond their means or they’re buried under a mound of student loans. Likewise, there are people like you who are in great financial shape without working a traditional job.

I think you can keep your message straightforward. When someone asks you what you do, try something like: “I worked in X industry for a number of years, but I’m in such a solid position that I decided to quit my job to focus on my daughters for now.”

Someone who respects your boundaries will accept that this is what you’re comfortable sharing in the moment. You don’t owe anyone more than that. If they pressure you for more specifics, treat it as a big red flag. It’s pretty invasive to ask someone you barely know or haven’t met how they pay their bills.

If you’re using dating apps, try taking the lead when you match with someone. Ask him about one of his pictures, or mention something the two of you have in common. Often, we default to work talk when we don’t have anything else to talk about. The same applies if you meet a guy IRL who you’d be interested in going on a date with. Try to establish rapport before you exchange “What do you dos?”

If you’re on the apps, you could also mention a few things on your profile that convey financial stability without directly saying, “My life is not a dumpster fire.” For example, you could say that you just bought a home or ask for travel tips for a vacation you have planned.

I understand why you wouldn’t want to bring up the fact that you’re a widow during an initial conversation with someone. You’ve endured a heartbreaking loss. But it’s inevitable that this will come up relatively soon. That may not be such a bad thing. If a guy can’t handle the emotional baggage, it’s best to find out soon, before you’ve invested significant time and energy.

Robin Hartill is a certified financial planner and a senior writer at The Penny Hoarder. Send your tricky money questions to [email protected].