TIL "late in life" is late 20s.
keep your goals simple. Your first date is just there to see if you're gonna get a second date. You don't have to convince the other person to spend the rest of their life with you..


My best advice is do something simple that you enjoy. I've always gone to a restaurant that I thoroughly enjoy because I could if had the worse date of my life, but the night is still a win due to you going to your place.

My example? There is a little Taco stand near Venice beach in LA. I LOVE their carnitas. I can take someone there, talk and get to know them. If we hit it off, awesome. If we don't? Still awesome because I got my tacos.

There is no need to have an extravagant dinner or a whole evening plan for a first date. You are trying to get to get to know a person, no need to give your best capabilities on the first shot. Might as well make it a win for you regardless.


As a mid-late twenties professional predominantly aiming to date other professionals, I always aimed for 6-630 after work drinks. That way, if the date is going well, and you can turn it into dinner, or you can beg off as "have to do xyz tonight" after an hour or so.

Coming straight from work for the both of you can also provide a decent basis for a conversation. Mine usually went something like "how was your day > work in general > travelling for work> travel in general > hobbies outside of work". I probably had 10-15 of these first dates.


I think this is good advice for anyone but if you don't know the person very well, for a first date, I would suggest getting coffee or ice cream. Do not go out for dinner or something that takes long because if you realize within the first five minutes you don't like them, it's going to be really hard for you to escape. Getting coffee can be short and sweet but if you're really feeling them, you can then suggest doing something longer.


Go for coffee but have something nearby you could go do if you're both feeling it. Be it a walk in a park to feed ducks or laser tag. If you're both having fun see if she wants to go do whatever it is nearby. If you're not into it just end it at coffee.


I never use my phone on a date, but I still remember my first date with my current girlfriend we went to a brewpub to try some craft beers while we met, and I use UnTappd to check in beers I've tried.

Eventually it was bugging me so I asked if she'd mind if "I used my phone to check-" and she interrupted me to finish "check in beers! Shit I forgot I have to do that!" And she opened the app too.

Amusing that the one time I used my phone on a first date was the best one I was ever on. Obviously it was special circumstances.


To further expand on this concept. A lot of guys tend to become really nervous on the first date (I do it as well) because they want to impress the girl and want to be sure she likes them. If you think about it, the first date exist to be see if you like each other. Putting yourself in the mindset of “let’s see if I like HER” removes a lot of pressure from yourself, which will likely lead to you being less nervous and to a better date overall.


Be comfortable. Know what you want out of life and be willing to openly share your philosophies and passions.

Most importantly ask her a lot of questions about herself and make sure to listen well. Ask relevant follow ups and challenge her.


Don't go overboard on the compliments, especially in regards to her appearance. It comes off really strong and it a big turn off for a lot of women. And NO sexual jokes/comments.


I find that when it comes to your late 20s, the intentions of the people you are dating can wildly differ. Some people are dating because they want to settle down quickly (get married in a year or less), and others are dating more casually. It's best to figure out what you want and what the other person wants as well as soon as you can.

Also, as long as they don't have an allergy, find a good cologne.


You don't deserve them, they deserve you. In other words, don't put the other person on a pedestal. Just be yourself, if it doesn't work out then they would have been a bad fit anyway.

Worst thing you can do is get yourself in a hopeless relationship because you act like somebody you aren't during a date.


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