Updates: “Too Old to be Crushing Like This” Responds

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.

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If you have a relationship/dating question I can help answer, you can send me your letters at [email protected].


  1. Bummer that it didn’t work out, but I think it was good that you took the opportunity to get to know him as an adult and made the decision that he wasn’t the one for you. It’s better than always wondering ‘what if’

    ps- I love updates. All you LWs out there, SEND UPDATES!

  2. Grilledcheesecalliope says:

    Bummer, but that sounds like a whole lot of no. Glad you still have your friend.

  3. He sounds like a real peach.

    Oh well, at least you don’t have any “what if?” regrets. Maybe that alone is worth $100.

  4. lets_be_honest says:

    Hey, good for you for giving it a shot. Sounds like a total dirtbag when it comes to “loans” though.

  5. karenwalker says:

    Well, at least you gave it a shot and can move on without wondering “what if.” I’m glad to hear that even though things didn’t work out with Max, your friendship with Mary is unaffected.

    I would maybe try contacting him once more asking for your money back. Keep it simple and say something like: “Hey Max, Mary told me you got a new job. Congratulations! Now that you have a source of income, it’s time for you to repay me the $100 I lent to you to turn your phone back on. I’d like a check by March 10th. Thanks!”

  6. Well, it’s too bad it didn’t work out, but at least you know. And, I’d definitely ask to be reimbursed. It’s pretty shameful that he hasn’t already sent you a check.

  7. John Rohan says:

    As someone who strongly leans to the political right on most issues, unless he advocated killing all illegal immigrants, I take exception that such people are “lacking in basic empathy”.

    To me the bigger red flag was him not wanting his mom to know he was dating you. WTH? It could mean he is seeing someone else, someone who has met his mom already.

    And as far as him not paying for dates – even in my college days when I was very poor, I just couldn’t stand for the woman to pay. But there are so many ways to go on dates for free or low-cost (beach, picnic, friend’s party, cooking for you at home, etc), that he could have treated you if he cared enough to get creative about it.

    1. yeah i agree with you. it sounds like he was very childish but at least she tried it out

    2. tbrucemom says:

      Thank you for your reply. I also lean right and was taken aback by the “lacking in basic empathy” comment too. Considering his other issues that would be the last thing I would worry about. I’m not going to go on a political rant because that’s not what this letter was about, but I do get annyoed when people making those kind of comments just because you have a differing opinion.

      1. Lily in NYC says:

        I see your point, but we really don’t know what the guy said – From what she wrote, it seemed clear to me she was being diplomatic and his leanings were more of the “damn immigrants wanting amnesty and damn f*gs wanting marriage equality” type than just a difference of political ideology.

  8. Avatar photo Addie Pray says:

    He sounds horrible. Glad you figured it out in a few dates and not longer. But I think you should get your money back. … Now. Ask for it, then update us again, ok?

  9. Well in some ways, it’s probably better that the mismatch was so clear and apparent. It’s the murky grey middle areas that tend to get us in trouble because they can drag out into months/years of uncertainty. Sometimes the “romantic” nostalgia of our past can blind us. Our brains have an innate desire to close circles and make links with past and present. In the story of your life, discovering a romance with Max might have seemed like a satisfying ending to a sad tale. A Hollywood style ending meant to give John’s death some meaning. Or something.

    I’m glad you avoided falling into that plot line. The rekindled friendship with John’s sister sounds like all the healing and reconnection that’s needed. And for the cost of $100, at least you have the comfort in knowing that you helped out his little brother too….

  10. I love Jess’s advice above…I myself fall into the murky grey areas and try SO HARD to make something work because there’s no-one else on the horizon and the comfort factor is nice.

    I applaud you for seeing the differences and for not hanging onto him, brava!

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