She won’t wait around forever
"Laura" and I have a strong connection and have known each other for 12 years. We have seen each other out socially, but due to our schedules, I mostly see her when she's working. When I go to her job, she asks me to sit where we can see each other. We've shared dinners while she works. She laughs and pretends not to listen to my conversations with other customers, but sometimes she joins in. We've talked about going away together (we even joked about taking our significant others on a group trip, before we both became single). I think we would be great together, but I wouldn't be able to provide for her; I'm still rebuilding from a failed business endeavor. She has been dropping hints about not waiting around forever, but I can't give her what she needs right now and the pressure is too much.
I do think this could work once I can establish my new business and don't have to worry about taking time away during the critical start-up phase, which, for now, takes all my time. She has children from prior marriage, but I do not. We are both in 40s.
How should I bring up and deal with this issue? I know I'm ready to get married ...
You're fantasizing about marrying this woman, but it doesn't sound like you've had any real dates. You've barely seen her outside of work. Your expectations are way too high.
Instead of preparing yourself for a life with her, why don't you start with dinner? Find out if she's interested in some social time. You can take one night away from your new business to see if the chemistry is really there.
If she doesn't accept your offer, reevaluate the whole thing and accept that this might be a flirty friendship that doesn't need to evolve. Respect whatever boundaries she sets.
But if she does make herself available, know this: You can date her even if you're not a perfect version of yourself. You don't have to "provide for her"; it sounds like she's capable of taking care of her own family.
You can also talk to her about your concerns and explain where you are in your business life (assuming she's interested). It helps to be transparent. It saves time – and prevents a lot of guessing and heartache.
Readers? Should the LW wait to pursue this until the business is in a better place?
"Start on step one and go out on a date with her. She has a job so you don't have to provide for her." – sunalsorises