What’s appropriate first-date attire?

After a few good phone conversations, we agreed to meet for afternoon coffee. It was a beautiful perfect-weather day, so I decided to wear a cute summer outfit.  I spent an hour taking a shower, dressing and getting my cute on.

Arriving early, I staked out an outdoor table at the coffee shop. He called to say he just drove by and was parking. That was thoughtful.

So imagine was surprise when he walked up in work-out shorts, t-shirt and sneakers. He obviously didn’t spend a nano-second thinking about first impressions. He knew I was a successful businesswoman. Did he think he would be appealing in this get-up? Or did he think one shouldn’t care how others decide to dress?

While one could argue that it’s shallow to care what others wear, it does set a tone. If one looks like they take pride in their appearance and desires to put their best foot forward, people notice. If one spends a little time deciding how to best show that they put some care into their presentation, it contributes to a positive first impression.

He was smart, articulate, nice and pleasant looking. He asked me questions about myself, but some were the same questions he asked yesterday on the phone. However, it was clear we had different world views, and he admitted he was broke.

So the quandary — since there was nothing odious, do I see him again? Or do I not waste each others time because it’s clear that there’s no long-term potential?

How have you handled such quandaries? See the person again or not?

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14 responses to “What’s appropriate first-date attire?”

  1. Joan Price Avatar

    No, I don’t think you should see him again, because his world and yours are too different. If he’s broke, dresses for the gym when he’s going on a date, and has a different world view, would you be happy with him? If not, why waste your time?

  2. Marie Avatar

    I say don’t see him again. He would probably hit you up for money down the road — since you would be his girlfriend. It would cause resentment & lack of respect for him on your part. If he’s truly broke, you’ll end up paying for any activities you do together.

  3. Monu Avatar

    I think you should not at all mind the first impression. It is a petty thing compared to your chemistry, compatibility and comfort with him.

  4. Brenda Avatar

    I would not see him again. If you have no long term potential with him and that is important for you, I would NOT waste another second with him.

    His choice of attire (which it looks like he put no thought into) makes me think that he would act similarly for other dates/events/ etc. It also says to me that he might be a man who is socially clueless.

  5. Heather Avatar

    I would say that if you decided on the first date that you had different world views, there is going to be little compatibility. Sometimes chemistry can get in the way of noticing these things, but it didn’t, so I would go with your gut. You would be wasting your time and his.

  6. Wendy Avatar

    I wouldn’t see him again. I agree—different world views and I don’t like that he asked the same questions again. I agree with Brenda–don’t like men who are socially clueless.

  7. Lisa Avatar

    While sloppy clothing in a middle aged man is a turn off, it would matter more to me that he was broke. Even if something out of his control made him broke, he is still broke, and you would have to pay for everything. That would get old after a while. I think the fact that he is broke and still showed up in shabby clothes– not making any effort to impress — would be a turn off.

    But who can say. We can all wait forever for the perfect person. I might go out with someone like that one more time if he was really smart and funny and thoughful just to get a more complete picture, but I would not do the initiating–or the paying! And if he showed up in running clothes again, I would run for the exit….

  8. Dating Goddess Avatar

    Looks like the consensus is to not go further. Immediately after the date, he’d texted “Thank you again. It was nice chatting with you. I hope we get a chance to do it again soon.” To which I said “Yes, agreed” He replied later, “Are you really interested in seeing me again or were you just being considerate?”

    The last missive came in at the end of the evening so I decided to craft a more thorough text in the morning. I told him the parts I liked about him, and said my hesitation was that we seemed to be in different places in our lives. I was wanting a partner to travel the world with and he had different priorities for his time and money. I said it would be frustrating if we got close then saw how different our needs were.

    I haven’t heard from him, but I didn’t really expect to.

  9. Lisa Avatar

    DG..You made the right choice. It can be tempting to give someone who you sense has issues but is at least pleasant to talk to a second chance, but that has never worked in my experience. I once met someone for coffee who also ended up being broke–he had created himself to be a self employed artist. After 2 seconds, I knew the meeting was a mistake. He was very odd and was wearing some goofy outfit that reminded me of the Sgt Pepper album. Needless to say, I tried to be polite for 30 minutes then had to flee. He sent me this pathetic email about a year later pleading with me to help him find a job. So many mid life men need social workers and not dates.
    If you ever read the online paper The Onion, check out the newest edition. It has a funny story about a woman’s mind working hard to justify all her date’s flaws!

  10. Petya Avatar

    I really must to point my mom’s attention at this blog, definitely! You girls give the knowledge and advice necessary to be dating goddess after 40!
    For me is like travelling in the future, or having nice adventure!

  11. Sue Avatar

    We each have a limited amount of time and energy each day. If there is no potential, I would suggest not seeing hum again. The great news is each date that is not a fit for one reason or another, brings greater clarity to the qualities we do want to attract.

  12. Devadasi Avatar

    As the first meeting was successful, I definitely would suggest to see the person again..

  13. James Avatar

    Awesome Article, Sounds Lovely 🙂

  14. Richard W Avatar
    Richard W

    Oh, this is a little difficult. I always believe that if you are unsure of a date, and cannot make up your mind, you should stick to the three date rule. If you still don’t know after three dates, then I think it will usually be a dead end!