Monday Manswers: “How do I handle the dreaded first date?”

Let’s face it – men are terrorized by the idea of planning a date. Countless questions pop into our mind giving us “Date Hate” such as:

  • “What do I wear?”
  • “Where do I go?”
  • “What if I run out of things to say?” 

    The dreaded 4 letter "D" word

Fear no more, as I am going to give you some foolproof tips to ensure that you get what you want. First, I don’t mean that – get your mind of the gutter. What I mean is that you should want to gauge how well you get along with your date in order to move to a second date or to remain friends (or acquaintances).  Now, I am going to assume two things:

  1. You actually like this girl (or guy, not to be exclusive here)
  2. You are genuinely interested in taking things farther than a second date
  3. You are going on a dinner date

With respect to point 3, there are tons of options for first dates that are far more creative than a dinner date, but since it’s the most common, I’m going to tackle it here in this piece. You’ll have to follow my blog a little longer for me to divulge some great date ideas later. Now hit the jump for my foolproof guide to dating mastery!

First, let’s go over some pre-date pointers.

Where do I take her?

  • Pick a nice restaurant that you have been to before, and where you know some of the bartenders or waitresses. This will make you feel a little more comfortable. You will also assume a measure of control because she is coming into your “territory.”
  • Make sure the spot has a lot of hustle ‘n’ bustle (I’ll explain why later) – it’s pretty much a given to choose either a Friday or Saturday. I personally would go with Friday since I find it to be a more lively night. 


  • It’s extra cushy if you find a place with a distinctive feature. The key here is activities. The more there is to do, the less awkward silences you may have to endure if you are taciturn and reserved. Thumbs up for sushi bars (sake bombs, loud sushi chefs), places with hookah (interesting experience), and Spanish tapas bars (sangria, old Latino people dancing, a band). You get the idea – the more there is to do, the less you have to do.

What do I wear?

Obviously, this depends on where you go, but that’s why YOU pick so that you know how formal it is and relay it to your date. I would avoid belligerently luxurious places on your first date because then how do top it if things go further? Also, don’t take her to Taco Bell. Strike a nice balance here. Given this, here’s what to wear:

  • Dark, fitted denim
  • A white or black button up is always acceptable and sexy.
  • Don’t wear some bright red shirt just to impress your date. Plus, what if she hates red?
  • For the love of all humanity, please wear some nice shoes! This is a terrible faux pas I see guys make all the time! Girls LOOK at your shoes. Shoes are her favorite thing in the world – you don’t think she is going to look at yours? Clean and polish them a bit too.
  • If it’s cold, wear a nice blazer or v-neck sweater over this ensemble and you’re ready to go. A simple, timeless, classic outfit with no fuss or frills. 

    LeBron's Date Outfit

Do I get flowers? Optional, I think. But if you do, I’d only do it if you are going to her place to pick her up (awkward to give in a restaurant, then she has to carry it all the way home). Also, I would go for a single flower on the first date instead of a bouquet. Why? Personal preference, but again, I don’t like to go overboard here. And don’t get a rose if you do – it’s so cliche.


A personal favorite - the Stargazer Lily


Now, here’s some “on the date” tips to impress your gal:

Act like this is a special occasion:

  • Make reservations at the restaurant.
  • Open doors for her. 

    Social Lubrication

  • Order a bottle of wine – a waiter at Taco Cabana once gave me some priceless dating advice. In regards to buying drinks, he said, “Don’t ask! Just get it, man!” This means don’t ask her what bottle she wants, just order one you like and share. She’s not going to know what to get and most women are indecisive when it comes to ordering anyways. Look at the menu beforehand and pick one out or talk to a waiter or sommelier and ask what’s good.
  • Get dessert! Why not? You only live once – plus most women love chocolate, especially on special occasions.

I need to take an aside to point out things to avoid!

  • Don’t overdo it – do nice things but don’t act like she is above you by any means.
  • Don’t act nervous and indecisive. Again, that’s why I mentioned earlier that you should pick a familiar location.

Next, let’s move to the middle of the date:

Get the most out of your conversations:

  • Don’t bore the girl with talking about your job or other mundane topics. Let her do most of the talking so that you learn more about her. Remember, you want to see how compatible you are with her!
  • Spruce up the conversation – talk about fun topics. Social dynamics are a great topic since all people, and especially girls, love to give input on how they view certain social situations. For instance, you can talk about your friend who is a crazy, stage 5 clinger on guys she dates. Your date will get a laugh (hopefully – if not, then YOU have the stage 5 clinger)
  • Eyes up, not down: Actively LISTEN to her so that you can react and respond to the words coming out of her mouth. It’s rude to ignore what your date is saying. Think about the attention you want when you are trying to make a point to someone and mimic this when someone else is speaking to you. 

    Don't do this.



As the movie Van Wilder taught us – “first dates ARE interviews.” You need to find out if you want to pursue a relationship after this night – if you don’t, you may just be wasting your time.

What to do if you run out of things to say:

  • The reason I suggested a happenin’ place is that people watching is endless amounts of fun.
  • Point out the girls sitting at the bar waiting for guys to come buy them drinks. Play a game with your date where you try to figure out who is on a date. Then, try to figure out if they like each other or if it’s a terrible date. Laugh at the drunken, old married couple doing the tango to the band. Make the restaurant your own little board game.
  • Take her to the dance floor (if there is one). Sometimes, you need to let your body do the talking.

Do I pay for the bill? Yes. I’m all for parity, but it was your idea to ask her out, so you should pay. And tip well too.

What should I keep in mind? Be confident, smile, laugh, and be yourself.

So get out there and become a dashing, debonair date!


About Fab Manual

Men's Fashion Blogger
This entry was posted in Etiquette, Manswers and tagged , , . Bookmark the permalink.

5 Responses to Monday Manswers: “How do I handle the dreaded first date?”

  1. Rania says:

    Hahaha I love the “spot girls who are waiting for men to buy them drinks” — ull see that everywhere so that’s always a sure hitter.

    Bravo on the blog as always

  2. This could even work for guys of my age, sixty plus. I will ask my wife first for a date before asking a stranger for a date. LOL. I will let you know how it goes.

  3. Vivek says:

    HAHA! My dad just asked my mom out on a date…she said no. Poor guy.

  4. Booman says:

    In the eloquent words of one of our generations greatest thinkers: giggity

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