When I asked Lori what was new in her life this last week, I had no idea she was dating! But I could not be more impressed with her level of self-awareness about money, and the feelings that she has concerning money in this relationship. Lori has hit one of the proverbial financial nails on its head, and I am so glad she is sharing it: Sharing our personal financial histories and, in particular, failings has to rank as one of the most difficult (and unfortunately easy to disguise) topics for new and not-so-new couples. No good can come of it.
The first thing I would say to Lori is, "You are not alone." Everyone, E-V-E-R-Y-O-N-E, has experienced financial setbacks and made money mistakes. Lori ought to be very very proud of all that she has accomplished -- warts and all. If someone tells you they haven’t made any mistakes or have no anxiety about money, run.
It's absolutely critical to be open about her current situation, her feelings about it, and any anxiety that their disparate financial conditions creates for her. I am not saying she needs to exchange credit reports and 1040’s with everyone she dates. Her financial situation and life experiences are, however, an important part of who she is and feeling comfortable in her own skin around someone she's dating is absolutely a big deal.
I have worked with many couples whose financial difficulties were largely caused by a lack of communication about money. Again, personal finance is probably not a good lead-off topic on the first few dates, but it is important that Lori and her new boyfriend share openly and honestly. It sets the level of disclosure and honesty that you expect, and will in turn embrace.
As to how to begin the conversation: Lori, start by handing him this post you have written. Your concerns are straightforward and clearly come from your heart. Let him read it when you know you'll both have time to discuss it. His reaction and the discussion that follows will tell you, I believe, much of what you are seeking to know about him and his views.
Financial conversations can be difficult even when couples have had a long history of good communication. I encourage you to stretch, as you said, out of your comfort zone and take the initiative to get the answers to the questions you are asking. They are great questions, Lori. They are the right questions.
On a personal note, I am really thrilled, challenged and honored to be working with Lori. (Thank you Lori!) Her challenges remind me why a life-centered approach to financial planning is the focus of my practice.