by Tamar Caspi 
under
Relationships
Dear Tamar,
I met a wonderful woman on 100hookup. 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.
by Tamar Caspi under
Relationships
Advice that people always give engaged and newly married couples is that they have to be transparent about finances. Money is often cited as the reason for a marriage’s demise. I do not think people should post what they make on their 100hookup profiles for many reasons (you are still a stranger at this point, you don’t want to be pre-judged, it’s no one’s business) but there are conversations you can have while dating. You need to know how your date views and values certain jobs. Teachers work hard but don’t make a lot of money – what does your date think of that? Does he or she value teachers? What about people who are born into a lucrative family business where a generous salary is imminent – does your date resent you for that? Does he or she feel it was unearned? These are serious questions that need to be asked. Again, a number doesn’t necessarily need to be divulged as no one needs to see your bank account statements yet, but knowing whether or not your date respects your line of work is important.
Once you are in a serious relationship that is headed for the chuppah, you need to have the talk including income. Are you going to combine bank accounts or keep separate accounts with a joint family account? Who is going to pay for what? Will you divide it based on percentage of income earned or will you pool everything and not think about it? When you have children, is someone going to stay home and will the other person respect that decision, including the lack of income (not to mention appreciating the unpaid job of being a stay-at-home parent)?
This is just the tip of the iceberg when it comes to talking about money, but don’t avoid the conversation otherwise it will come back to bite you.
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