I (M29) have been dating someone (F29) over the last month (NYC). She has been asking me deep questions about lifestyle and future goals, and I can sense she wants a relationship. I really like her, but it's still early enough to cut things off.

The biggest red flag is financial (and therefore lifestyle) incompatibility.

  • She has complained that she doesn't get paid enough at her non-profit. I'm guessing she makes $60-80k.
  • She has mentioned that she has student loan debt (2 degrees). Her degrees aren't in a field where you can demand high salary from what I know (some general liberal arts degrees).
  • She's considering going to law school ($$$). Afterwards, she wants to work on abolishing the death penalty, which she's very passionate about. I'm concerned that she's putting herself into a deeper financial hole.
  • She wants to move into a 1 BR here (NYC), which would probably be around $2000-3000 in the neighborhood she wants to live in.

On the other hand, I live with 2 friends (roommates) and make $135k / year. I got this job after getting laid off & I'm underpaid, and I'm pretty confident in 1-2 years I can make $200-300k + / year, if the job market improves, based on what my peers in NYC are earning in my role.

I make sure to save money in my 401k, IRA, and Brokerage accounts every month. I stick to a budget and consider myself financial savvy. I want to purchase a home at some point and retire before 60.

I have no idea what her financial situation is, but I have a feeling that it's not great. And that there's no plan to really fix that.

  1. How do I bring this up with her? She has asked me some very deep questions so I feel like it's not that crazy to ask.
  2. How would you handle this situation? I think 10k debt with a plan to pay it off is different than 100k debt. Both scary though.


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