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 JeremySpoke under
Date Night,
Single Life
I went on the last date of my life last night. That is usually the sentence of somebody that just found the love of their life, or somebody that decided to actually do something with their life like serve in the military. I said it, however, because I am tired of trying my damn best to only get abandoned an hour in.
I think I’m a pretty good looking guy, and I also have a pretty good personality. I just don’t know how to be on a date. I just don’t. After a good amount of failures, I realized that I was too excitable. So then, I toned it down, but I think I was still smiling too much. She would tell me about her brother with cancer, and I would continue smiling and shaking my head like an idiot. People generally like people that are happy, but you have to be able to also convey other emotions appropriate to the situation. So I finally managed to not wildly scream and flail my hands the whole time, but I was still too damn happy, trying way too hard to be likable.
But girls don’t like likable guys. They like assholes, and I’m not one. I spend my whole life pretending to be happy. That is, while around other people. In my car, or in my room, I’m the angriest person on the planet. At work, however, or on a date, I’m the happiest. I think I need to find a medium, but it doesn’t really matter because I’m not going out on another date. At least not in the near future. I need confidence, and I’m not going to get that by constantly watching women in front of me make excuses for why they have to leave. I need to do things that I’m good at, like being early to things or parallel parking.
I’m really good at parallel parking. A great date for me would be just driving back and forth in and out of a parallel parking-style spot while the date is in the passenger’s seat. I wouldn’t talk, because that never works out for me. I also won’t have any music on, because I have a horrible taste in music. Just me, and her, parallel parking. I am just now realizing while writing this that this can be construed as a sexual metaphor. It’s not. It’s really the only thing I’m good at, and I thought writing this paragraph combining parallel parking and dating would be funny. It’s not. I don’t care.
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