The Dating Engineer Blog

Helping you optimize your love life.

The Ultimate First Date Guide For Men

Jan 29, 2024

Although I provide a lot of online dating tips, much of my advice applies to all kinds of dating. Whether you met the girl online or in-person, this article will give you a framework for an ideal first date.

For online dating in particular, first dates should be a breeze. If you’ve done everything properly up until this point (including having a fun phone/video call with her- a subject I will cover in another article), she should already be highly attracted to and invested in you.

1. Pick a Time & Location

As the man, you should be suggesting the time and location of the first date almost 100% of the time. Do your best to never plan a first date more than 72 hours in the future. We are all highly distractible these days. The more time there is between confirmation of plans and the date, the higher the chances of the girl flaking.

Note: If you met the girl in a dating app and had a really good phone/video call before arranging the date (as I always recommend), the chances of her flaking are reduced to almost zero.

Never do dinner as a first date.

The first date should be simple and low commitment for many reasons:

  1. If there’s no chemistry, it’s easy to bail. This shouldn’t be an issue if you have a call before the date.
  2. It saves you time/money. You barely know this girl and shouldn’t be investing much into her until you’re sure she’s worth it.
  3. It shows her you’re not trying to win her over. Women, especially the most attractive women, are used to guys trying to impress them. By not doing that, you show her that you know your own worth and she hasn’t won you over just because she’s hot.

The ideal location is somewhere you can easily talk and preferably sit beside each other rather than across. Bars are the obvious choice, as long as they are not loud. Drinking alcohol is always optional.

I advise against doing something more active like an activity or going for a walk. When you’re not facing each other, it’s harder to connect and build up chemistry through touching and eye contact.

You also want to pick a place that has a second location nearby that you can take the girl to, preferably walking distance. We’ll touch on this later in this article. If you want to do something active, this is where you’d plan that. Or it can be another place to keep talking. All that matters is that you change the location.

2. The Day Of

Again, if you’ve had a good call with a girl and planned the date not too far in advance, you shouldn’t need to worry about flaking. However, it’s good to verify that she is still committed by sending a text the day of the date reaffirming the plans.

This also helps her feel more secure, because women get flaked on as well. It demonstrates social aptitude and reliability. It suggests she can trust you, and building trust with a woman is extremely important.

I won’t go much into detail about the obvious stuff, but make sure you shower, shave, brush your teeth, wear nice, clean clothes… you know, basic hygiene.

You might be a little nervous. That’s totally normal. The more dates you go on, the less nervous you’ll be. Not sure if I’ve mentioned having a phone/video call with the girl before the first date, but it also helps to alleviate nervousness for both people. Also keep in mind that she’s agreed to the date so she’s already into you.

Do whatever you need to do to get pumped up and confident. Remember: you are not trying to win her over. You shouldn’t be hoping she likes you. You should be hoping that she ends up being cool enough for you want to spend time with her. She needs to win you over. If things don’t go well, it’s fine because it just means the two of you aren’t compatible. You have tons of options out there.

3. Arrival

Make sure you’re on time or even a few minutes early. Once again, we want to establish reliability and trustworthiness.

When you see her, smile, and give her a hug. If you have a hard time making conversations with girls “more than friendly,” you can also give her a small kiss on the cheek which will immediately make things more than friendly.

Feel free to compliment and/or playfully tease her. Whatever feels natural to you. Then lead her inside.

One thing you’ll notice if you follow me is that I’m strongly in favor of a reasonable amount of chivalry. Don’t go over the top with it (ie, don’t bring flowers on the first date), but small things like holding the door, walking between her and the street, etc. really help to build trust and attraction. I’ll write another article on this later.

Open the door for her, and let her go in before you. As she passes you, you can touch the small of her back to initiate more physical contact. If the opportunity to pull her chair/stool out is there, go for it.

When sitting down with her, do your best to sit beside or perpendicular to her. If you sit across, it’s okay, but it will be more difficult to increase physical contact. If a host(ess) is leading you to a seat, don’t be afraid to ask for a more optimal spot if you see one. Assertive behavior like that is very attractive.

4. Conversation

You’re sitting down and the conversation begins.

Throughout the night, make sure you maintain strong eye contact with her. Don’t be creepy about it- you can look away every now and then and be sure to smile, but you want to maintain more eye contact than you normally do.

As for the conversation, a little bit of small talk may come up, but in general, try to avoid it. Have a few really deep, interesting questions prepared to ask her to help yourself avoid defaulting to small talk questions (what do you do, how do you like living here, what do you do for fun, etc).

Here is my biggest tool for transforming any conversation from boring to interesting: why?

Asking “why?” can instantly turn any conversation deep. You don’t want to sound like a 4 year old asking the word “why?” over and over again, but really try to dig into her answers to get to the substantive reason behind them. That’s how you truly get to know a person and make them feel listened to and understood.

The art of conversation with a girl is another article topic (or three), but overall, try make sure you keep it deep, fun, and most importantly, flirty. Don’t make the mistake that so many guys do of playing it safe and just having friendly conversation the whole time. And don't spend the date trying to impress her. 

Challenge her. Talk about hypothetical, romantic situations with the two of you. Tease her. Compliment her. Touch her.

If you do all of the above in a socially calibrated way, she won’t want the night to end.

5. Location Change

Changing locations is an essential part of the first date, especially if you sense that she could be open to going home with you at the end of the night. It adds a touch of spontaneity and adventurousness to the night, and makes the date seem longer. Again, very few guys go outside of scheduled plans and move girls to secondary locations without discussing it beforehand.

As mentioned earlier, you should already have the second location (or even several options) picked out to transition her to. It could be another bar, a club, an arcade, a movie, ax throwing, etc. If you’ve built up enough attraction and comfort with her, it’s okay for the second location to involve an activity that is more active than just talking.

They have done studies that show fear activates the same part of the brain as love, so if you do an activity that gets the blood pumping, that can be extremely powerful for attraction. I’m not recommending sneaking onto a building rooftop but...

6. Escalation

Ideally you will have at least held her hand some during the first part of the date, but if the opportunity wasn’t there, that’s okay. However, you definitely want to increase physical contact at least a little bit on this second half of the date to avoid the, "you're nice but I don't feel the chemistry" text the next day.

If you’re looking for a serious relationship (or if you’re just really shy) and want to go slowly, that’s totally fine. Take her to a movie and hold her hand during a romantic part.

If you’re looking to move things more quickly, take her somewhere higher energy where you can get physical more quickly.

If you’re planning on trying to take her home with you and you haven’t kissed her yet at the first location, you certainly need to at the second. In general, the more, the better, along with heavy touching, but it’s not 100% necessary.

With all of this, it’s important to read her vibe. Some girls will be fine with getting wild in public and then going home with you. Some prefer to be more subtle, but will still go home with you, even if you’ve only lightly kissed on your date. Some girls are impossible to sleep with on the first date, so you’ll have to be patient and wait. However, in general, the more patiently you behave, the shorter you’ll have to wait ;)

7. Ending the Date

Time to say goodbye. If don’t have plans to sleep with her on this date, walk her to door/train/car/etc. Tell her you enjoyed the date, and give her a kiss. If you want to take things super slowly, a kiss on the cheek is fine.

If you are going to try and sleep with her, you need to give her an excuse to agree to come to your home. This is a tricky subject that requires its own article, but women experience a lot of pressure from society that can make it hard for them to agree to come with you, even if they want to.

The excuse can be as simple as having a glass of wine. Or something interesting that you want to show her (ideally that you’ve brought up earlier in the evening). Or meeting your dog.

Feel free to be a little bit persistent. Most girls will require a bit of coaxing, but of course, no means no, so don’t be too pushy. If you can sense she’s into you, but she is being resistant to sleeping with you on the first date, be very chill about it and don’t push her. If she doesn’t feel pressured, there’s a very high chance she’ll agree to come home with you on the next date.

What comes after you’re inside is a subject for another time.

Getting a girl to agree to a first date is easier said than done. If you want to learn how to consistently get girlfriend-quality women on first dates, enter your email address below.

Once you have mastered getting girls on dates, and then mastered the dates themselves, you will truly be able to have any type of dating life you want. Whether that means casually dating as many women as you can or seriously dating beautiful, intelligent women until you find the one you see a future with (or both), the world will be yours.

Until next time.

-Coley

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