It’s time again for “Dear Wendy Updates,” a feature where people I’ve given advice to in the past let us know whether they followed the advice and how they’re doing now. Today, we hear from “Too Old to be Crushing Like This” who wondered if it would be inappropriate to date the brother of her high school boyfriend who died over 12 years ago. They’d met up again recently at a birthday party and sparks flew, despite their six-year age difference. Keep readind to see if they went out.
I went ahead and went on a few dates with Max. It became apparent that we were just in totally different stages of our lives, just as you predicted could be a conflict that came along with an age gap. He was going through a temporary period of unemployment after having been laid off last summer. Not that unemployment itself is a reason not to date someone, but I will admit that being the only one doing all the driving and paying for the 4 dates we did go on was a bit irritating to me. He also leaned too far to the right on several political issues such as immigration, social safety nets, LGBT rights, and how “his” taxes should be spent. I don’t think differences in political views alone should be a deal breaker for everyone, but it is something I personally take strongly into consideration when contemplating starting a relationship with someone. In my personal opinion, a person who leans that far to the right is lacking in basic empathy.
The final straw in making my determination of his “datability” happened when I was dropping him off at home after our last date. He asked me to drop him off around the corner from his house because he was worried that his mom might see me dropping him off, and he didn’t want to have to explain to her that we had been hanging out. Hopefully, I don’t need to justify why this irked me – because I can’t. It bothered me. It just did.
To make a long story even longer, during our last date he explained that his cell phone had been turned off (he had been messaging me thru facebook for a few days) because he didn’t have the money to pay the bill. He was worried that he would miss a job opportunity because potential employers wouldn’t be able to get in touch with him. I offered to let him borrow $100 on the condition that he paid me back from his first paycheck after he found a job. He sent me a text the next afternoon to confirm that his phone was back on and to thank me for the small loan. I responded with a simple “you’re welcome” and haven’t heard from him since. I have not attempted to contact him, either. Mary told me that he found a job 6 weeks ago, but I still have yet to hear from him, let alone get my money back.
Well, in the end, I guess it was better to have gotten to know Max a little more and find out that, although we were very strongly attracted to each other, we just weren’t compatible. At least I don’t have to wonder “what if?” forever. I wish I could have given you a much steamier update, but it is what it is. Luckily, none of this had any impact on my friendship with Mary, whatsoever. We are still great friends, and we continue to take our lunch breaks together and hang out on weekends.
Thank you, and the DW community, for giving me the push to go ahead and go out with Max even though it didn’t work out in the end.
Thanks for the update! Glad to hear you have some resolution on the matter.
If you’re someone I’ve given advice to in the past, I’d love to hear from you, too. Email me at [email protected] with a link to the original post, and let me know whether you followed the advice and how you’re doing now.
You can follow me on Facebook here and sign up for my weekly newsletter here.
If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].