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First 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.

Notes

• 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?

First 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.

Notes

• 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…

First 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.

Ever worry about being incompetent when it comes to pleasing your partner? People weren’t born knowing the dos and don’ts of affection. It’s something that takes practice if you plan on being good at it. At first it may be awkward, but it’s worth it in the long run. Here, WC gives you pointers on things to do-and not do-when with your partner.

Kissing/Making Out

Kissing is wonderful. The best kinds of kisses tend to be between two people with mutual feelings for each other. It can be a simple peck to say “good morning,” or it could be steamy and head-spinning number that leads to much more. Regardless of the purpose of your kiss, there are some things you should keep in mind:

Vary the intensity of the kisses.

Soft, light kisses make the body tingle; hard, passionate kisses make heads spin. Don’t keep the same pace the whole time or your partner will likely become uninterested. Keep her excited by combining slow kisses with fast kisses, shorter kisses with longer ones, and by adding some nibbling here and there. She’ll melt.

Don’t leave kissing for just the lips.

It gets boring and won’t get your partner as excited as if you switched it up. However, try not to go for the R-Rated spots just yet. A kiss on the cheek or the forehead will have her anticipating a slow, romantic time, whereas a kiss to the neck or the ear gets things hotter.

Easy with the tongue.

It’s common for people to get excited and want to use whatever means to get closer and make contact with even more of their partner’s body, but when it comes to making out, try to keep it simple. Ease into it and try not to use your tongue too early or too much; with making out, it’s best to keep things simple. Use that energy for other things, like what often follows making out.

Pay attention to her reactions.

Does she try to back away from you when you press hard? Take the hint and back off. Does she push her lips firmer against yours when you’re kissing her softly? Take the hint and kiss harder. Listen to her breathing when you’re kissing, too; heavier breathing means she’s enjoying herself; sighing means she’s really feeling the kiss for more than just lips touching lips. Things like yawning may mean you should try a different approach.

Touching/Fondling

One of the five senses, “touch” is a very powerful way of connecting with others. Touching one’s arm while talking to them shows interest, a quick massage can relax and revitalize someone, and a caress can send shivers to every inch of a person if done appropriately. In order to help you determine how befitting yours are, we have these pointers:

Never have idle hands.

When kissing, pulling her into you closer by the back of the head, around the waist, or at her butt will get things amped up. Running your hands up and down her arms or holding her tight are big pleasers as well.

Massages are wonderful.

You don’t have to lay her down and bust out a towel, hot stones, and massage oils, but nothing sets the mood quite like a massage. Pressing into her and making small circles with your fingers will loosen her up and relax her. When you’re done, she’s likely to return the favor. Never rush massages, though; you could end up hurting her, which is never good.

Don’t use the “milking a cow” technique. Ever.

Yes, breasts are pretty fun, but never under any circumstances pull them (unless you’re involved in a BDSM deal, in which case you probably wouldn’t be reading this anyways). Keep in mind that smaller breasts tend to be more sensitive than larger ones, but all of them have nerves. Please respect that. Otherwise we may try the “technique” on you.

Don’t rub too hard for too long, especially if it’s dry contact.

If you’re playing with her breasts and rolling her nipples between your fingers or similar, please, please, please be soft. If you use too much pressure, especially when it’s dry skin touching dry skin, you will cause a burning sensation, chaffing, and/or bleeding. The pain is unbelievable, especially when she goes to put a piece of clothing on over them. Keep things at least somewhat wet so no irritation will follow.

Oral

Giving-

Giving oral to a girl can either be for her sheer pleasure and a way of getting her to orgasm, or as a way to prepare her for intercourse. Depending on your situation, different things are okay to do. The following pertain mostly to the times when your goal is to simply please her:

Start things off right.

The first few brushes will be the most intense because her body will be just starting to warm up. Take advantage of that and be slow and methodical with your strokes. Also, keep away from the clitoris until she’s fully ready; premature taction can cause pain and discomfort, two common mood-killers.

No biting.

At least, not hard biting, and not right away. Nibbling should be done after your partner is pretty turned on, otherwise her body will be too sensitive and it will cause pain. Suck and lick her for a while before using teeth.

Don’t get bored and give up.

The average woman takes about twice as long as the average man to reach orgasm. Maybe you climaxed after 5 or 6 minutes of her giving, but don’t expect her to always do the same. Maybe your tongue and mouth get tired; that’s what you use fingers for. Never rest your head on her thigh because you’re tired. She’ll be distracted and offended by the contact, resulting in even more time to get her to orgasm. In other words, if you think you might be giving oral in the near future, be rested and ready for about 15+ minutes of (highly rewarding) work.

Don’t start kissing immediately after cunnilingus.

Most girls find their scent and taste to be disgusting and have no interest in tasting it from your mouth. In time, they probably won’t notice it too much, but it’s always welcomed for you to take a drink of water or something before kissing. However, there are some girls that have no problem with it, and some even get turned on by it. Just play it safe at first, or better yet, ask her.

Receiving-

It’s a common misconception that all girls despise giving blowjobs. While some may be uncomfortable with it, others want to make you one happy camper and enjoy either the act of giving it or the fact that they can make you so happy from something. Be respectful and follow these little rules and you’re sure to have your partner coming back for more:

Relax.

If you’re tense and unfocused, you’ll kill the mood. The more relaxed and at ease you are, the easier it is for your partner to get comfortable and concentrate on pleasuring you as much as possible.

Don’t force her head to take too much.

Sure, it’s pretty common for guys put their hands on the back of girls’ heads when receiving oral, but things like ‘gag reflexes’ do indeed exist. Let your partner decide how much of you they can handle at a time. If she can take it all with ease? Luck you, you get to be deep-throated. If she can’t? That’s quite an ego boost to know you’re too big for her to take.

Hold her hair.

Hair gets in the way of the giver. It can get in your partner’s mouth, causing her to gag or stop things while trying to fix her hair. Or, if she has to use her own hands to hold it back, that could take away from the pleasure; those hands could be touching you! By holding her hair back, it shows that you’re getting into it and that you care enough to help her. Plus, it lets you see everything that’s going on better. You know you want to.

Give her a warning when you’re about to orgasm.

Surprises are great and all, but when it comes to orgasms it’s best to just tell her.
It’s the polite thing to do, and it gives her a chance to decide what to do when it hits.

Intercourse

Having sex is part physical, but most of it is how well two (sometimes more, but that’s separate) people connect. If you’re having sex with someone, it means you trust them to a degree. It also means you’re both interested in pleasing yourselves and each other. To help you out, we have some things to remember:

Don’t be silent.

Feedback is key when it comes to just about everything, especially sex. Like the way she swivels her hips when you’re inside her? Tell her! Don’t like her heels digging into you? Also tell her, but in a constructive manner, like putting her feet somewhere else and then raving about how great it feels.

Don’t fake pleasure.

Moaning, screaming, panting, and calling out her name are all absolutely fantastic, but only when you mean it. Not only will she probably know you’re faking, but lying to her is one of the cruelest things you could do.

Do what’s in the best interest of you and your partner, and know your limits.

Sometimes going at it hard will be exactly what you want to do, but only do things you know your partner can handle. If she’s tiny or weak, it would be in your best interest not to pound her senseless into a wall. If she’s big or strong, you’ll need to use a bit more energy to make sure she’s enjoying it.

Be open about your likes and dislikes, and be sure to know your partner’s.

This changes partner-to-partner. Maybe your last girl liked things slow and soft, but your new girl may want her hair pulled and to be spanked. Being open with each other makes things more satisfying overall when you’re together. Bonus: when you talk about it, you’ll probably both be ready to get behind closed doors and start trying things out! Make sure you know her stance on experimentation, too; maybe you’re jonesing for anal, but you better know how your partner feels incase her backdoor is off-limits.

I’ve had two successful, laid-back dates with a great girl. After the second one, I walked her up to her porch, but didn’t make a move to kiss her. It felt like I missed a chance – I was getting a good vibe from her. Was I too timid? Should I definitely make a move next time (providing it feels right)?

This is one of those really really really tough questions.

Short answer? There is no way to determine when you should kiss. It’s a spur-of-the-moment thing.

Long answer? There isn’t a way to determine when you should kiss, mainly because every girl is different, especially when it comes to stuff like this. Some girls (the more reserved ones, mainly) tend to have a general idea of a number of dates or “time” when it is right- some girls don’t kiss (or screw, for some) before the third date, others do. This also compounds when you take into consideration that she might just not be feeling it, or she may BE feeling it and you just don’t- something like that.

My advice? Go for it, but try to read in beforehand. Is she responsive and close to you? Girls who stay far away from you (i.e. don’t touch you, don’t stay near you while walking, are afraid of grazing against you) are not going to want to be kissed- at least, not too quickly. However, if she’s displaying obvious signs of attraction (lingering, looking at you, not carrying an extreme sense of personal space), you can go for it.

Yes, this is difficult. Everyone has this trouble. I’m not the type to advise asking beforehand (for some, it may be cute, for others, it may be creepy), but just try to be careful and do it right. And make it unexpected, too, that’s always fun for them.