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Modern Dating Advice For Men & Women · Apr 24, 2026

First Date Observations: Red Flags, Etiquette, Manners & More

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Eddie Hernandez · Modern Dating Advice For Men & Women

I was recently interviewed for an article on food and dating for a publication, and luckily, my answers were not included in it. The whole idea of assessing a red flag based on what someone orders, let alone a chicken breast, seems a bit absurd, but unfortunately, there are many people out there who have dismissed profiles, matches, date ideas and 2nd dates for much less.

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Being nervous is normal but it’s even more challenging given how people meet these days: online. Before apps, people would meet at bars, cafes, restaurants, events, social clubs and have 5-10 minutes to screen people before exhanging info and agreeing to go out on a date. These days, too many people skip that crucial part and either do it via texting, video chats or meet for the first on a first date after meet on dating apps.

The perceived efficiency of apps, and casting a wider net is offset with less real-time, in-person, timely information as people photoshop images, use outdated photos, take images from weird/high angles to slim their looks or materially change their appearance even in a short period of time 6-12 months.

What makes dating even worse is that people can’t even agree on proper etiquette for creating a profile or even heading into a first date.

There are lots of (strong) opinions on first dates but if you approach it with some basic rules and guidelines, one can reduce bad first dates and wasted time but don’t expect to eliminate them completely - it comes with the territory.

If a person has a wide range of photos with different looks, look them up online, do a video chat, ask them which photo is the most recent, ask when they went on a trip (in said photo).

If you don’t want to be stuck on a boring dinner date, don’t accept them or initiate them. Go to a bar with food in case you get hungry or if things go well. Go out for a coffee, but at least make a walk/adventure out of it i.e. street art, explore a street fair, catch a farmers market or check out a pop-up market.

If you are not sure who sould pay, do counter payment, don’t go to a Michelin star restaurant - this stuff is pretty basic yet people still gripe about this in 2026. There are plenty of ways to have fun, creative, unique, romantic dates without breaking the bank but you have plan for it.

There are many things to observe when going on a first date including:

  • how the person treats hostesses, servers

  • if the person avoids entire neighborhoods or cities

  • if the person cancels a date and doesn’t suggest an alternative (whoever cancels, the onus is on that person to make new plans)

  • does the guy only suggest locations near their them (particurly where they live?)

  • does the guy get upset if you reject dinner, night time or dates with drinks in favor of coffee, daytime or something more casual?

Red flags are subjective, deal-breakers are not. Showing up drunk to an event, not making plans in a timely manner, showing up late without advance notice - these are all deal-breakers in my opinion but not everyone has these boundaries set nor maintains them. Sure, you want to give everyone the benefit of the doubt, but that benefit is extended within reason and for exceptions, not the norms of bad behavior, poor communication skills.

I’d argue not enough people are canceling dates or leaving early enough. Your time is the most precious thing you have and sticking around on a bad date, not only is a bad choice, but will likely increase the chances you sabotage future dates with increased jadedness.

  • If you are running late, let the person know asap not after when it’s a given.

  • If you are not able to give someone’s full attention, you are not ready to date.

    • Checking your phone, looking disinterested, giving one-word answers, not asking questions (or asking leading, distrusting questions) is guaranteed to kill any chances of a 2nd date.

  • If you have nothing to talk about, you are not ready to date. Having no friends, no hobbies, no ambition, nothing to offer the other person is selfish and a waste of time. No one is perfect but you should be on your way to self-impovement and having something to contribute to dates, conversation and each other and just expect to take, take, take.

Signs of a good first date are just temporary signs and not absolute truths - they are like markers on a hiking trail noting where you are but not an end point. Things like good communication, transparency, effort are needed for a good first date, not avoid chicken breast orders, liking the same shows or even having the same hobbies.

Yes, those things are nice but compatibility is often more about mindset, approach, outlook on life, rather than checking off boxes on a resume, dating profile.

A good first date may even be that you know for sure a second date is not needed. It means you are saving yourself from another unnecessary date, possibly one you may otherwise agree to because of lack of options, dry spell or because you are lonely.

Good first dates often involve some discussions, banter or even gaining insight into the other person. People often get fixated on 1-2 things but knowing what is a preference vs what is a deal-breaker is what really separates those who have success vs those who complain about others all the time.

  • Look like your photos on your dating profile.

  • Enjoy the date, have fun, be safe.

  • See if you want to see the person for a second date

    • Goal should not be to get other person to like you

  • See if you did not overlook any obvious red flags

  • Depending on timing, conversation, see if things like intentions, goals, lifestyles are compatible

  • Goal is not to pre-qualify someone too quickly, prematurely i.e. using a few compatible interests, vibes to overlook more deeper factors.

Read the original on moderndatingbyeddie.substack.com

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