Wellcultured - A men's fashion, fitness, sex, and lifestyle magazine.

The Ultimate First Date Guide

Written by admin, Friday, May 8th, 2009 in Dating Columns, Sex & Dating

first-date4First dates are hard. While they are technically supposed to be fun learning opportunities where two people get to connect and learn about one another, they invariably devolve, at least in the mind of the participants, into great peacocking shows- long worrisome exposes of your pros, the hiding of your cons, and the attempt to do everything “right”- though nothing ever goes perfectly right. Even the most talented, confident daters can experience a bad date or worry about making a date a bad one- it’s hard!

As many of you know, I’ve written previous guides along these lines for normal dating– but apparently, first dating is hard. First dates are oftentimes a completely different game- they can be difficult and end up going very well (serious connection with a girl culminating in a kiss), or really poorly (proverbially holding your head in your hands as your histrionic date talks about her ex boyfriends and texts them during the date (true story(!))). So, to help alleviate some worries, answer many e-mails I’ve gotten, and help out you in your next first date (that could always be your last first date!), here are some tips to make your first date the best damn first date ever.

Ground Rules

First off, let’s set off some overarching ground rules for your first date- from planning to the date itself.

Rule 1: No sex. I know this is a silly first rule to have, but virtually everyone in the dating community (who actually is part of the legitimate dating community) agrees with me: no sex on the first date, period. No nudity. Hell, even making out is pushing it. At most, a good date can end with a kiss- but said kiss should never be presumed to happen, but it should be the good ending of a great date- not the obligatory ending to a mediocre date.

Rule 2: Plan, plan, plan. Though it seems silly, plan out things if you can- but don’t make it obvious. Reserve the restaurant for the time of the date- and make sure your date can eat stuff off the menu. Plan a time in which your mind is free of outside worries. Obviously, have enough cash to pay for things. If she wants to go on a walk, try to know the surrounding area. While there is such a thing as over planning (never let your plans dominate the date- be flexible!), try to make things as easy as possible.

Rule 3: Show your best aspects, but learn more than tell. Of course, the idea here is to get to know your date. Be on your best behavior throughout the entire process- but really, worry less about talking/showing yourself and more about your date. Remember, she has as much of an onus to show you her worth as you do showing her your worth.

Rule 4: Keep yourself aloof, at least early on. No talking about marriage, your problems, or similar issues. Don’t show her to all of your friends, and don’t meet all of her friends. Don’t make long term promises. A first date is exploratory, not any indicator of marriage or something. Remember this.

Part 1: Prep Time

Okay, so, let’s hit the ground running. For the sake of making this a short article, I’m going to presume that somehow, you’ve found a girl, and you’re ready to ask her out on a date. Thankfully, you’ve done most of the work- pending the girl is telling the truth, she’s already shown enough interest to justify going on a date with you: you’re 75% of the way. The problem is, now, you have to pull out all the stops and amaze her with a great first date that will not only give her a taste of you, but leave her wanting at the same time.

First off, call her and make direct plans. Do not waffle, do not ask her what she “likes” or “wants”. Of course, you’ll want to have a few options- a few restaurants, a few movies or activity ideas, etc- but generally, the idea is to have things in mind and be confident in your ideas. Have a general idea of the menu, and ensure wherever you go has the opportunity for special diets (vegetarians/vegans, allergies, etc) to be accommodated. Plan a day, a time, and a location at minimum– basically, treat it like any other appointment you may have. Naturally, figure out transportation- figure out if you’ll pick her up (nice, but sometimes a bit intrusive for some girls), or if you’ll meet her there.

Second off, plan. Almost immediately when you hang up, make reservations for the restaurant you chose, if reservations are available. Buy tickets if you plan to go to a movie or show- most theaters make advance tickets available, even online. Clear plenty of time around the date, allowing you plenty of time to shower, dress, and devote your mind to the date. Basically, make all the calls necessary.

I can’t stress planning enough. Planning is what makes or breaks the logistics of a date. Right before the date, everything necessary should be fully prepared for to the best degree you can- virtually every part of you should be ready for the date, from head to toe and everything around you. You should have clothes ironed (if necessary), clean, and ready to go. You should be well groomed in every respect, from your hair to your finger/toenails to any stray body hair. Your car should be clean, if applicable, and obviously ready to make the drive to and from your date location. You should have all the cash you need to pay for the meal twice over, and then any accessory costs- be it dessert or just extra activities outside the main date. Obviously, if there is any sort of chance she may come to your place (not advisable), make sure your apartment/house is clean. In essence, you should be ready to make this date the best damn date ever- and you should do nothing to keep it from being as such.

Ideally, a date should be planned around something that you can do together, with plenty of chances to talk. Movie theaters are a poor choice. Talking over dinner, though stereotypical, is a great option, as it opens up plenty of discussion opportunities. Doing something like walking through a park is also a great option. Cooking classes and other fun, random endeavors are also fun, pending they don’t distract you/her too much. Avoid going overboard (keep the girl in her comfort zone- don’t take her off skydiving or something), and keep the date fun (no creepy “come-to-my-place-and-lets-talk” dates)- focus on conversation as much as you can and keep the activity light.

Despite all of this planning, be flexible. Understand your date, despite her interest in you, may not be able to commit to a ridiculously planned, demanding schedule. Don’t be miffed if she has to change dates or otherwise has to postpone the date- emergencies do come up. Obviously, don’t expect a date to go perfectly, either- though you want to make it such, perfect dates never exist, and you should be flexible enough to adapt to any sort of circumstance- be it a restaurant being full up, a car breakdown, rain, a movie theater breaking down, or that sort of thing. Ideally, the girl should never know you planned a lot, but it should show.

So far as what you should wear/be like, be yourself, but be yourself dressed up to a certain level. Even for a movie date, wear nice pants (nice jeans are okay in more casual situations), a good shirt, and good cologne. Shoes should be clean and usable, even for the longest of walks. Avoid ostentatious fashion or super-formal wear- stick with something fun and traditional, that shows yourself, but keeps you looking nice. Cologne, much like we’ve talked about on this website before, should be faint and nice. Avoid excessive gel or jewelry or anything- keep yourself simple, versatile, and fun.


  • Don’t take a girl standing you up beforehand too personally. While it obviously is the equivalent of a slap in the face and/or a kick in the groin, remember girls whom make dates and avoid them later should not be dated in the first place. As a general rule, give a girl two chances to move the date if she “can’t make it”- and if she clearly is not interested, then just ignore her and move on.
  • When you reserve a restaurant or buy a ticket, do so as early as possible. Good restaurants and movies fill up quickly, and it can often leave you unable to provide a date you “promised”. Strike early.
  • If you have to make changes, tell her ASAP. Treat a date somewhat like a business meeting- keep people posted. Don’t change things abruptly.
  • Plan to wear good clothing, especially good shoes. Many girls, who learned from their mothers, look to shoes for the quality of a man- and then, after that, they sometimes look at the style/brand of clothing he has on. Wear damn good shoes.
  • Speaking of clothing, prepare for the weather. Clothing should neither be too thin or too thick. Remember, no matter the season, it may rain, get suddenly cold/hot, or just become unpleasant. Wear something as much of in the “middle of the road” as possible.

Part 2: Date Time

So, it’s the day of the date, and everything’s going as planned. How do you keep the date going well?

couple-having-dinners600x600First off, remember, conversation is everything. If you prioritize anything, prioritize the ability to keep a conversation going. A good date will help this along, but even if she doesn’t, try your damnedest to keep her talking. Ask questions as much as possible- people love talking about themselves, so use that to your advantage. Without being stalker-ish, try to learn as much about your date (her interests/hobbies, her work/school, any animals she may have, her week, that sort of thing) and ask about them. Though it may be incredibly tempting, do NOT ramble about yourself- answer her questions and elaborate as necessary, but don’t spend too much time. Leave her wanting more information. If you have trouble talking- if she’s being difficult, or you just naturally have trouble in conversations period- ask questions and remain as light as possible. Oftentimes, there is no negative in honestly admitting you’re nervous/excited/naturally bad at conversations- don’t worry about admitting so.

Whatever you do, during conversation, remain yourself. Don’t fake anything. Don’t lie. Humans are inherently incredibly good at detecting lies and fakery, especially ham-handed attempts at being “cool”- so don’t even try it. Being yourself is more than sufficient for even the best girls in the world. Remember, the idea is for her to get to know you, not get to know who you want to be. Of course, you’ll want to be fun and interesting- don’t mope around and act boring just because that’s the “real” you- but be as true to yourself as possible.

Second off, make everything as easy and respectful as possible. This is where the planning comes into play. Your goal, as the male in the date, is to make the date as easy and worry free as possible: your date should not have to worry about anything at all. Pay for meals and other costs, if at all possible. Be kind to the waiter/waitress, and tip well. Ensure that she has what she needs- if it may rain, make sure you have an umbrella. Generally, remove the big questions from your date’s mind- she’ll thank you for it.

On top of this, exude manners like a refined gentleman. Hold doors- that includes car doors. Only begin eating after she begins eating. Avoid bad table manners. Use “please” and “thank you” as much as you can. Essentially, treat your date like a princess, no matter how silly it may be- it will not only impress her, but any of her friends. I’ve met a ridiculous amount of girls who have rules about the “quality” of guys as related to their manners in this regard- so brush up on your manners and knock her socks off. As silly as it may sound, most girls like to be treated like royalty at dates, as most dates are special to them- use this to your advantage.

Third off, end on a high note. This is where things get confusing, but important. After your date- after the movie, dinner, or whatever you have planned- remember to end on a high note and make her wanting more, not less. As I mentioned above, you want to have a clear, definitive ending to your date, leaving everything on a high note- not on a low note. Dinner dates, except uncommon ones, last about two to three hours: expect about that much, and no more, for a first date. Though she may be far too old for it, be sure to get her home before her “curfew”- don’t overextend your welcome, and make sure to give her plenty of opportunities to end it herself.

And, finally, the option of a kiss, a hug, or nothing at all. This is VERY dependent on the nature of the date (if it went well, if the girl is more open or not, etc), and it should entirely depend on how the flow is going. If the date is going incredibly well and you felt as if you connected well, going “in” for a kiss is a very viable option. However, hugging is fine too- and it is not an indication of disinterest or anything similar, so long as you aren’t cold about it. Play it by ear. I can’t give you a definitive answer- just go with the flow, and avoid being a pig. Just remember, no sex.


  • Remember, you always have the option to get out too- so don’t stress out too much. Your date has as much of a responsibility to impress you as you do her. You can easily choose to not see her again, rather than the other way around.
  • Focus on her. Eat lightly. Don’t zone her out and look around. Focus on her first, the food/movie/whatever second.
  • Be nice to everyone. Be nice to wait staff, employees, other people, and the like. Most girls watch this carefully.
  • Carry plenty of money and handle financial transactions discreetly for obvious reasons.
  • Turn your cell phone off. Under no circumstances should it ever be on during a date unless there is the potential for a massive emergency involving something only you could fix. Texting is tantamount to slapping your date in the face.
  • Avoid talking about anything inflammatory- ex-boyfriends/girlfriends, heavy political topics, etc. It is fine to talk about these in a joking, casual way, but no further. It is not fine to talk about religion, politics, ex-girlfriends/ex-boyfriends, personal problems (physical, mental, or otherwise), or other “heavy” topics. Leave these for subsequent dates and more private settings.
  • On this topic, just don’t talk about heavy sexual topics. She’ll know you’re sending out feelers.
  • PAY ATTENTION. You gain brownie points for actually remembering what she says.
  • A first date kiss should be simple, romantic, but without sexuality. Don’t oversell it. Don’t make out. A single kiss can leave her wanting a lot more.

Part 3: After the Date

After a date, don’t drop the ball. If the date went well, don’t forget to keep the ball rolling- you can easily do perfectly during the date and ruin it afterward!

Plan to call at least two days and not more than 7 days after the date. Don’t do it the hour after, nor would it be entirely advisable to do so the day after- not unless you stay in contact a lot anyway. Give her a little bit of time to process the date, then propose a second. Any more than 7 days and you’re making it clear you aren’t interested. You don’t really have to propose another date, of course- calling to say you really enjoyed the date is fine enough to leave your proverbial calling card.

No matter how well the date went, don’t run around like crazy making her your new “girlfriend in training”. Don’t go off and talk about her to all of your buddies, your family, and your coworkers incessantly. Have some restraint- too much expectation can be creepy. Of course, you can talk about her- she’ll be flattered- just avoid making the insinuation that her going on a date with you made you a “couple” of some sort.

Finally, make every next date that much better. Keep knocking her socks off. Don’t let the first date be the best she ever gets. Every date is a learning experience- so, as much as possible, learn about your date and make all subsequent dates better if at all possible. Girls hate guys who have one good date and then a series of uninspired, boring crap-fests.

In Closing…

WhisperFirst dates are scary for everyone-even myself, despite the irony of the fact I’m writing this article. The work of having to basically sell oneself- that is, to make oneself attractive to a potential mate for the very first time- is a very intimidating thing. Though planning and pracice help, nothing can truly prepare you for a good date quite like just being yourself- as being yourself allows you to really, truly connect with your date and develop a true relationship, not a feigned one.

Tags: , , , , , ,

12 Responses to The Ultimate First Date Guide

  1. pi4arctan1guy says:

    Yeah, just /b/ yourself.

  2. Tim says:

    How much do you take your own dating advice? Are you for real trying to tell us that you don’t make out with a girl on the first date if she is wants? Do you really call her if you had a good time? Sounds like your a hypocritical writer to me, Bro.

  3. TheAssofDink says:

    This actually helped me out. A lot. In my date. Not saying without this article, I would fail. This helped me understand more about the date and to nail the good points and avoid the more common bad points. Thanks again, Kirk.

  4. Jacob says:

    Nice article, helps understand a lot more.

    Thanks. 🙂

  5. hgu says:


  6. Nona says:

    best dates are unplanned and unscripted where anything goes

    this seems like a guide for 30+ y/o internet networking site daters

  7. Xanderholz says:

    I would like to ask, why are the shoes you wear specifically important? I understand why one should be stylish and wear clothes appropriate for the occasion, but why did you make a focus on shoes?

  8. JMN says:

    Regarding the first date kiss, I’ve found there to be a tremendous amount of potential with a simple kiss on the cheek. A kiss on the lips is conventional and easy to go awry, however, if you’ve been following this excellent guide, you’re going to come off as a gentleman, and there’s nothing that secures that impression faster than the respect of soft, platonic kiss on the cheek. Hell, I’ve had those turn into much, much more than a simple kiss – but the ball is in her court to do so.

  9. sam says:

    this is the most retarded advice I’ve seen on this site, and possibly the worst advice I’ve seen on a first date anywhere. it’s generic, bland and a sure-fire way to have a boring time ending in an anti-climactic good night kiss.

    women don’t want boring men who will just follow a cookie-cutter build. you have to be adventurous, exciting. and what’s the with the no sex rule? I almost ALWAYS fuck on the first date, granted they are 5-7 hour, full-day, engaging dates.

  10. RHM says:

    The law of supply and demand point out that scarcity can raise demand. Gold, oil, diamonds… If you make your self completely available to a woman, she can have you anytime SHE wants. How many times has a woman not been available when you had a free evening?

    Make yourself scarce to the girl. They call it playing hard to get. Too many guys jump at the chance to go on a date with a woman; and usually it is on the woman’s terms.

    The problem with dates…

    How many dating websites give you a list of creative dates, top ten date ideas, best dating ideas… as if a “date” was the magical key to any relationship.

    You’ll have a hard time wrapping your brain around this one if you haven’t been in a marriage or multi year co-habitation relationship. See if you can trust me on this one.

    Taking a woman on a date is the opposite of scarcity. Dates set the tone that “I must win that person over.” Notice that I said “person” instead of girl. I have no problem being treated to a nice dinner or movie; neither do most women.

    Winning the client – take them to lunch or dinner

    Winning the stranger – buy them a drink

    Winning the friend – bring them a gift

    Winning the girl – ______________

    How did you fill in the blank?

    It sets the tone for the relationship: always trying to win her over.

    Win her again and again with … better clothes, newer car, nicer house

    When do you finally win this game? Never. Many guys just try to get out, after realizing that she will never be content. Why do you think that financial problems are stated as a top reason for divorce?

    Never get into that game of winning her over.

    Don’t get me wrong, I want to enjoy the companionship and all the wonderful things about a woman… her perspective, her soft skin, her feminine mystique, her respect, kissing, etc. BUT

    My idea of a date, I cook for you or you cook for me. If she’s happy with that and treats me well, then we can consider going places.

    Make yourself scarce.


  11. Some Guy says:

    A friend of mine dated a guy who followed these rules. She got bored of him after about three dates.

    Women want to be treated like a princess … in moderation.

  12. Wallaby says:

    I came back to this article just to check and see if I was missing anything for a blind date tonight. While some of it is helpful, especially reminding me to reserve a table at our restaurant, I think following this guide to a T would be a big mistake. Here’s the basic formula: you are going out with this person to learn more about them. It’s an opportunity to have fun, not to overplan everything like a neurotic. All that other stuff is just fluff. You can’t possibly predict how your date is going to react to everything you do, so just play it natural.

    We can keep this article around as an example of “doin it wrong.”

Leave a Reply

Your email address will not be published. Required fields are marked *

  • Latest Question

    Should I go to a community college before I go to a 4-year college? Looks cheaper.

    Read our Answer More Questions and Answers Ask a Question
  • Latest Articles

  • Latest Discussion

  • About Wellcultured

    Well Cultured is a men's online magazine with advice and reviews on fashion, fitness, dating, lifestyle, and many other topics. About Us
  • http://www.wellcultured.com/feed">RSS Feed | Contact Us | Terms of Use/Privacy Policy
    WellCultured is powered by WordPress.