Tips For First Dates

Quick reference to what NOT to say or do.

Juliette’s First Date Advice: Written For Men, But Relevant To Women.


  1. Dress for the place you are going. And
  2. Dress like you are trying to impress a girl. Any girl. Every girl.

There is absolutely no reason to wear a hoodie and your oldest pair of shorts to a first date unless you are going kitesurfing (whatever that is) or tree climbing. If you are meeting in a lounge, wear a button up shirt. Even if you wear it with good jeans, you will look like you cared about looking good for her. Even if you only have t-shirts, wear your best t-shirt and wear non-jeans with it. Girls notice. Think about it, if the girl showed up wearing yoga pants and an oversized t-shirt you would probably not be terribly impressed. Consider that women also want to get an idea of what a man’s body type is. We as the fairer species don’t get the luxurious chance of having men turn up in a skin tight leg-showing, cleavage-advertising ensemble, so think about how you want to portray yourself. As a sweatpants-wearing hobo? Or a respectable, classy, sexy, confident guy.

For women: I live by the standard that if you dress promiscuously on the first date it will be assumed you are promiscuous. Good for you if you like to sleep with guys on their first date, I actually envy you a little bit, but I don’t/can’t/won’t. So I do not wear short skirts, I limit the cleavage, and I usually wear my hair down. I find that it successfully keeps men from making awkward premature advances. If you dress like a business lady (which I am) I usually get treated respectfully like one.

Also an important note to make for women on first dates, is not to go too over the top if you intend to see the man again. You don’t want to show him the best you’ve got on the first shot.  If we say that every woman is a 10 when she is looking her best, on the first date dress like a 7. On the second date, dress like an 8. On the third date show up as your 10 self and you decide by how much you like him or want to sleep with him when you bring out the short skirts and boob shirts.

Don’t get me wrong, I am not opposed to being a complete tease, but I have found that it is best for me to see what the guy is like first before bringing out the big guns (not that I have big guns). I get offended when men make sexual comments on first dates and a good way to avoid throwing away a nice guy who might have gotten the wrong impression is to dress a bit square on the first couple of dates.


Ask the girl. It is gentlemanly and thoughtful to let her choose where to go, especially if you have never met before. Maybe she is more comfortable playing mini golf, or in a crowded restaurant, or like me getting wasted on wine in a lounge. If she says she “doesn’t care”, take everything you know about her and deduce what is the best setting by that knowledge. If she likes fishing, offer to take her to do something where there is water. If she likes Thai food, offer to take her to a Thai restaurant. If she likes wine (like me! She is probably a champ you won’t want to mess this up with!) offer to take her to a wine bar. If she is shy, you might want to offer to break the getting-to-know-you ice in stages by taking her to theatre or a movie.

Note I wrote for each option “offer”. Don’t assume that just because she says she “doesn’t care” that it means she is up for anything, or likes surprises, or that she believes you will magically choose the right place. Maybe she does in fact believe that, but don’t set yourself up for disaster. For example if a guy took me to a steak house not knowing that I’m a vegetarian, I would be fine because I could choose other things on the menu, however he might feel stupid that he didn’t ask and then act like a self-conscious ass for the entire date. Make sure you decide together on the location.


If you met on a dating website, you should have at the very least a small list of a woman’s interests before you go out with her. If you get nervous before dates, make sure you go over the list before showing up for the date so you have a few things to ask her about. It is unbecoming to be overly nervous so if you have a few tricks up your conversational sleeve to talk about, you will be able to relax.

If you met elsewhere, no problem. People like to talk about themselves. As long as your date has average social skills, it should be easy to ask questions and let her talk about the things she knows and likes. as she answers the questions you can chime in your commonalities and your own stories. Here are the absolute most bare bones questions you can ask:

Where do you work?

What do you like the most about your job?

Do you ever think about doing anything else for a living?

What do you do in your free time?

Do you play any sports or are you athletic in any way?

Are you creative or musical?

What are your favorite movies/TV shows/music?

Where did you grow up?

Do you have any brothers and sisters?

Have you traveled much?

Where do you want to travel to?

All of these are easy not-too-personal questions you can ask to hear what the person is all about. I have a problem with overly shy people or people who don’t engage themselves into a conversation easily. I talk a lot so I have a pretty easy time meeting new people, but that doesn’t mean I constantly want to be filling in gaps when my date isn’t picking up where I left off. I am of course a special case, but it can’t be that uncommon that if you are awkward on a first date, you aren’t getting another one.

Lastly, don’t talk about sex. That proverbial ball is in the woman’s court, and if she brings it up you can gauge for yourself how intensely she wants to discuss it, and how much you want to reciprocate. But beware of talking about things you don’t want to or didn’t mean to that you may be judged by during your first impression. I once went on a date where somehow it kept coming up that the guy sometimes sleeps with girls on the first dates when they initiate it. Well, that guy got judged up and down by me because I don’t do stuff like that and it made him seem like a slut. Avoid sex talk until you know her a little bit better.


Chances are it won’t be the end of the world if you are a few minutes late, except that it will result in your first ever conversation with the new girl being on the subject of being late. Think about how you screw up any meeting where the first thing you have to talk about is why you weren’t there on time. Even if you are only going to be two minutes late, call ahead and warn her so you don’t have to talk about it when you meet in person.


Almost all women go on dates expecting to pay their own way. I personally have absolutely no problem paying for my own drinks when I go out, but I think a very good indication of whether the guy likes me or not, is when he pays the bill. It gives me a chance to smile and thank him and feel all warm and fuzzy at the end of the date, which is THE most important part of the date to make a girl feel that way.

I have met guys who have experienced women refusing to allow them to pay because they think them paying the bill implies that they owe them something. Well, I would laugh in the face of any guy who thought I owed him anything after spending ten bucks on me. Even fifty. Not many guys would actually have the balls to say it even if they did think so, therefore it is perfectly fine not to mention anything about it and just accept your thank you in whichever form it presents itself in.

Another comment I heard from a man was that he didn’t want the woman to think he was old-fashioned or chauvinistic. I’m sure there are probably a few ladies out there who feel very strongly about their independence that they would not accept a date to pay for them, but I  believe that there are not that many. Paying the bill is something people should let themselves be treated to whether it is your mom, your friend, your boss, or your date. A woman can always decline your offer and choose to pay for herself if she wants to and I think the most chivalrous and stand-up way to end your date is by behaving as though you really like her. That is, if you DO like her. If you didn’t like her, I think an excellent way to show this is by paying your own way, leaving the rest of the bill to her and get out of there.

Also, like it or not, if you don’t pick up the bill you are going to seem cheap. And in my personal opinion, generally speaking in all facets of life, cheap people are really unattractive. Cheapness and sexiness do not go together, so be sexy.

If you are interested in seeing a woman again, pick up the bill. If she is interested in you, and if she happens to be as honorable as me, she will try to pick it up next time.


It is my firm belief that if a woman wants you to kiss her, she will act like it. If a girl is gazing into your eyes and facing you, or getting closer to you or isn’t talking anymore but is still standing beside/in front of you, she is probably waiting for you to make a move. If she is avoiding eye contact, not even looking in your direction, you are getting zero readings from her body language, she is talking a mile a minute trying to fill in the awkward silences, she is probably just trying to get out of there.

Just because a woman doesn’t kiss you on the first date, it doesn’t mean she doesn’t like you, it could just mean she is not sure yet, or she simply doesn’t kiss on the first date as a rule. Make no assumptions about the missing kiss until you ask her on a second and a third date. Usually if you have not kissed by the end of the third date, it is expected that there will never be a kiss. The dreaded “friend zone” is likely to be your future dwelling by the end of date three if no move is made, so if you are not sure about the signals but you want to go for it, you pretty much have nothing to lose other than your spot in the friend zone anyway. You decide if the risk is worth the loss of friendship.


Read my own stories of train wrecks, crash and burn victims, and a few decent ones HERE

Read real questions from my readers and my clever responses HERE