Dear Tamar,

I met a wonderful woman on JDate. We got along wonderfully at dinner, but something came up in conversation that really makes me think there could be a serious problem down the road. We are both nearing retirement and began discussing our ”Bucket List.” As it turns out, she, a widow, aside from having a successful career of her own, was married to a very wealthy man. This man left her a huge estate. Her “List” included the kinds of things one would expect to see on it: vacations, cruises, etc. As for me, I am a middle-management guy for a major company and am planning to retire on a pension, Social Security and a modest 401k. Get the picture? See the problem? There is no way I can afford to live in her world.

Again, we really hit it off, and I would like to pursue this relationship, but can this ever go anywhere? What’s your advice?

Dear Financially Fraught,

Don’t make any assumptions. Your date may have been trying to impress you or she may want to indulge you by taking you with her on these trips. The best thing to do would be to be honest — tell her basically what you told me: you feel a connection and want to see where the relationship can go but you’re concerned that your idea of retirement is not aligned with hers. Let her know that you want to enjoy retirement with a partner but don’t want to put pressure on either of you to not enjoy life the way you had expected. All in all, the person you spend that time with is what counts, not what you’re doing, so hopefully you’ll get the answer from her that you’re hoping for.

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