So, that initial connection turned into a real date. She said yes. Congratulations!
Now what?
Let’s face it, first dates are all about first impressions. You know you’ve got to bring your A game. There’s probably a ton of questions flooding into your mind right about now:
1. Do I need to have a plan?
As the guy, there is an expectation that you should have some sort of plan for the date. That doesn’t mean you need to be the douchey guy who drags his date around from one place to another without her input and then tries to order food for her. Not cool.
But you also don’t want to be that guy who has no suggestions. “I don’t know. Whatever sounds good to you…”
The best way to strike a balance between those two extremes is to have some ideas and propose them. “I was thinking we could meet up for a drink at that [charmingful place], then take a walk along the [view-tastic locale]. How does that sound?” The idea is to be assertive and have an opinion, but to check in with her to make sure she’s onboard.
Ideally you want to plan the date so it has a fixed beginning and end. If the date is going well you can always add onto it. Or if it’s not a love connection then you can easily wind it down without it being awkward.
Remember, the plan is just there to provide some structure. You can always diverge from it if you find the date is going another direction.
It’s a good idea to have a few extra ideas for “add-on” activities in case you do find that that things are going well. When she asks “what do you want to do now?”, it is SO much more suave when you have a quick answer: “Well, we could go get an ice cream. There’s a great gelato place around the corner that I’ve been dying to try.”
2. Where should I take her? What should we do?
First dates are interesting because most likely don’t know each other very well. So, it’s a good idea to give yourself a situation where you can actually talk.
Maybe you can use those tickets to the death metal show for your roommate and figure out something else for the date with the new hot chick. I’m just sayin’…
But there’s no reason to stick with the traditional dinner or drinks. In fact, some seasoned daters have told me they like to work up to dinner—saving it for the second or third date.
While you want to be able to chat, it’s not a bad idea to choose a setting where there’s some sort of activity or shared experience. Like going to a wine or cheese tasting, going on a day hike or to the zoo. Depending on the girl and your sense of adventure, you can get pretty creative here. Hell, you could even go to Sears and have your portraits done. You’ve got to admit, it would be memorable.
You might think that doing an activity slows you down from getting to know each other. But actually, having some sort of shared “adventure” may be a better way to see whether you click with that person or not.
You find out pretty quickly whether they appreciate some of the same things you do or not. Do you laugh at the same things? Are you able to work together as a team?
When it works out well, you quickly forge a bond where it seems like it’s “the two of you against the world”. You both were brave enough to eat the really smelly cheese at the cheese tasting. And you both laughed when the actor split his pants during the play. Or you both found it entertaining talking to that bum in front of the museum who said he was an amateur painter himself….
On the flip side, activity dates can be useful even when you realize that you don’t have a connection. If there aren’t obvious sparks flying, it gives you something to do together so you’re not just awkwardly sitting across from each other with nothing to say. Worst case, you end up spending a couple hours with someone who’s not going to be a love connection—but hey, at least you both got something out of the activity, right?
3. What should I wear?
You should go naked. Totally in the buff. If she can’t appreciate the body that God gave you, then it’s just not right.
No, actually clothes are a good thing. Let’s face it, at this stage in your relationship both of you have to judge a book by its cover. So, even if it seems superficial, it actually is important.
On a basic level, you need to show you made an EFFORT to clean up. If you look like you slept in your clothes and you didn’t even bother doing your hair, your date’s going to notice.
As far as what you wear, obviously, you should take into account what you’re going to be doing on the date. If you’ve decided on a day hike, you probably want to avoid wearing those spiffy Italian loafers. But at least make sure you’re wearing your nice fleece and you’re sporting some decent hiking boots.
On the other hand, if you’ve decided to go to the opera, I think you can balls out with a full suit.
I think it’s generally it’s ok to err on the side of being more dressed up. Worst case, she might tease you about being a diva. And you can have a shared laugh about how you spend hours in front of the mirror or polishing your shoes with a 1-inch cloth made from 600 thread count egyptian cotton.
But you certainly don’t want to be so awkwardly dressed up that you look you’re about to do her taxes, or you’re headed to your first job interview in your “big boy suit.”
Fortunately, there are ways that you can dress up “casual” pretty easily. Even you if you decide to just wear a nice pair of jeans, you pretty much can’t go wrong with adding a sport coat and some nicely polished leather shoes with a matching(ish) belt. The steam iron is your friend here, as well as your lint roller (not to mention your razer/facial hair trimmer and nail clippers).
Also, hopefully it goes without saying, but this should not be one of those times you do the ol’ college “spray and walk-through” trick with your deodorant because you don’t have a fresh pair of pants. It’s your first date. For godsake, you both deserve a fresh start.
4. Should I bring flowers?
Great question! Just the fact that you were thinking about that shows that you’re a gentleman at heart.
That being said—and this may be controversial to some other aspiring gents out there—I believe you should NOT bring flowers to a first date.
Unless you’ve known her for a while before dating, I think it’s better to show up flower-free on the first date.
Why?
Because with certain girls it can be misinterpreted as being overly anxious or overly formal. What says “polite, classic chivalry” to you, might say “I’m desperately in love with you and I’m ready to ask your dad about the dowry situation” to her.
Just like you, some girls can also be a little self-conscious on the first date, and making them carry flowers around only makes it worse.
I think it’s much safer to bring flowers for a second date, since you’ve already had a chance to feel out how she might react.
5. How much should I be drinking?
Remember, the goal of a first date is to get so hammered that you drool on her at some point and she has to hold you up when you’re walking out. No, wait. That is NOT what you want to be doing.
Some veteran daters I’ve spoken with actually recommend avoiding alcohol altogether on a first date. For one, incorporating alcohol usually changes the timing of the date. But more importantly, it may keep you from being clear-headed when you’re just getting to know each other.
Honestly, there’s no rule about how much you should drink. The most important thing to remember is: make sure you’re pacing yourself with her.
You should not be racing ahead of her even though it may seem tempting if you’re feeling nervous. Try to resist the urge of chugging the glass of Bordeaux when it arrives at your table. Also resist the urge to have an extra shot of “liquid courage” before bringing back your drinks from the bar.
6. Can I be myself?
The best advice I’ve heard in this area—and it applies to a lot of other situations in life—is this:
Be yourself. Just be a better version of yourself.
What does that mean?
It means you shouldn’t try to contrive an alter ego for yourself. Don’t be afraid to talk about your real interests. To share your real thoughts—at least most of them.
But you need to have a pretty good filter. That means not telling the entire story of your life at the first sitting. For instance, talking about how one summer you had to have a boil lanced off your buttocks is NOT first date material.
Or, it’s okay to admit you like video games if the topic comes up. But she doesn’t need to know that you spent all of last Saturday unshowered, playing Mortal Combat in your whitey tighties with the curtains drawn, eating only Cool Ranch Doritos and some stale Peeps.
Give her a chance to see your other redeeming qualities before you lay that one on her.
Or, it’s okay to admit that you like romantic comedies, and that you’ve read AND seen Nicholas Sparks’ masterwork, the Notebook. But maybe you don’t need to admit that you cried for like 30 minutes afterwards. Not quite yet.
Being on your best behavior also means staying present, and trying to be mindful of common courtesies like not being on your phone. Nothing is more annoying than you pulling out your phone mid-date and saying “Huh huh, my buddy totally just checked in at [X] on foursquare. That place is so killer.”
7. What will we talk about?
For many people, the idea of spending 2 hours alone with someone they’ve never really spoken with is mortifying. What if the conversation runs dry?
To help yourself out, it’s not a bad idea to have a few conversation starters in your back pocket. You can keep a mental list of 3-5 things you want to her ask her about.
But you have to be careful to avoid the “interview date.” It’s no fun to be on the receiving end of a series of 20 questions that sound like someone’s just checking off a survey.
One of the best ways to strike a balance here is to avoid asking too many things that just sound like factual “stats” (i.e. what do you do, etc). It’s nice to talk about thing that you know will lead to more conversation instead of just “uh, I have 2 brothers.” Things like “what do you dream about doing?” or “what are you passionate about?” And make sure you know a few things for those questions as well. Especially with those topics, you’re going to need to be prepared to share.
As far as topics to avoid:
It’s not a bad thing for you to mention your friends—it’s sort of “social proof”. She’s thinking, “well, I know this guy has at least 2 friends. He can’t be a total axe murderer.” But you also want to avoid talking about your friends the entire time. Especially if one of them is a woman. The last thing you want is for your date to be thinking “who is this SANDRA person? I think he might be in love with her.”
Personally, I also think it’s a little tasteless to bring up the dating scene or to talk about other dates while you’re on a first date.
Above all, remember that your goal here should be to try and listen more than you talk. And if both of you are trying to do this, you’re likely in for some good conversation.
8. Should I ask her out again during the date?
This is just a feel thing. Only you can make the call on this.
Let’s think about pros and cons either way:
If it’s going great and it’s obviously a love connection, it can seem totally natural to ask her out again towards the middle or the end of the date.
But if you’re still feeling each other out, it’s not a bad idea to wait. The cons to asking in this situation are that: (1) you may be jumping the gun—maybe too fast too soon. (2) and most importantly, you stop being in the moment of the date.
You start to go into “mind montage” mode.
Maybe in your head you’re already flashing forward to her walking down the aisle towards you, and to your 2 perfectly proportioned and well-mannered children—who, oddly, yet so cutely speak in British accents (hey, don’t ask me, this is your montage!).
It’s great that you’re excited. But you’ve still got to be on your game for your first date and make sure you’re fully present rather than making plans for the future.
9. Should I pay?
Yes. Even she offers, insist on paying this first time. And in this day and age, she generally should at least offer. But don’t let her pay this time.
10. Should I go in for the kiss?
Short answer? Yes.
Longer answer: if you want to kiss her, you should probably try if you’re feeling like she’s open to it. Don’t go in with your tongue ready to swashbuckle; just go in for the peck, and if something more happens it’s all upside from there.
Sure, there’s the chance that she’s not going to be ready. And she may say “oh, not yet.” or she may turn her face and you get a mouthful of cheek. Do not be discouraged. This doesn’t necessarily mean she’s not into you. In fact, she might be waiting because she wants to take it slow—she might think once she kisses you, you’ll have her down to just her panties in just 30 seconds. And that’s awkward when her roommates are watching through the curtains…
11. Should I call her the next day?
There are certain dates where you both just know that it’s not a love connection and that you’re not going to go out again. For those, it’s okay to just let time pass and not reach out.
I once went on a first date where the girl fell asleep during a movie we were watching. And it wasn’t because she was tired from being a med student working crazy shifts saving lives, or because she had exerted herself by doing crossfit or something. She just wasn’t engaged. And it was pretty mutual. When we said goodbye, we both knew we wouldn’t see each other again. No biggie.
But what if you want to see her again?
Sadly, the “3-day rule” seems to have pervaded our culture. You may think that’s a good amount of time to wait before calling. Or if the movie “Swingers” is your dating advice source, you might think it’s a cool to wait 6 days.
Both of these are too long.
It used to be that you could wait a few days before calling. But now, everything is accelerated with the speed of technology.
Forget about the 3-day rule.
If you like her, you should definitely reach out the next day. But I don’t think it’s a bad idea to just text for that initial follow-up.
The important thing is that you make contact quickly. If you are radio silent in the first 24 to 48 hours, the girl will go through all the various worst-case scenarios in her mind, and will have basically already broken up with you before you get back to her. And six days? By then, she’ll have already gone out with and dumped somebody else.
So, I think the best mix is to shoot her a quick text the next day letting her know you had a great time. And then follow up day later with a call.
Or if you really like her and you’re feeling confident, give her a call the next day. Why not? Sure, if you’re both on the fence about each other, then calling too soon may ruin your chances of seeing her again. “Playing it cool” can work, but really it’s best for those situations where you haven’t made a love connection. But if she’s into you, she’s not going to care if you call her the next day—she’s going to be excited.
Did I miss anything? If you have any other tips for first dates, I’d love to hear them. Please leave a comment below!
