The Before, During, and After of a Great First Date
Here at SG HQ, our mission is to help you guys look, feel, and act your best. Sometimes, that means skincare tips or a virtual styling session. Other times, it’s helping you navigate what it means to be a gentleman in the modern world.
Your Best Behavior is a column for men by women about this intersection of style and culture.
If you’ve googled “how to ask a girl out” or “what to text a girl,” then you’ve inevitably come across an absolute avalanche of bro-centric websites promising can’t-miss tactics for guys on picking up chicks and getting laid.
I’m going to be honest with you:
The tips on these websites have definitely not been vetted by living, breathing women.
So if you’re currently reading this, the good news is you’ve already done one thing right.
You’ve come to the source—aka, living breathing women—for dating advice.
The pickup artist culture pushed by dating websites for single straight guys can feel really toxic, and the last thing you want to do is give a girl the ick before you’ve even taken her out.
Style Girlfriend, on the other hand is comprised of a team of women who want to help guys look, feel, and act their best.
We’re not here to stroke your ego, help you “trick” women, or make ourselves sound cool.
So I’m here to share some advice on first dates that will work.
And look, women are not a monolith (my first piece of wisdom!), but there are some basic tips for dating that transcend all the different kinds of women you might encounter.
Below, #SGapproved first date tips for men:
BEFORE A FIRST DATE
1. Take initiative, not control, when planning a first date
Two things immediately turn me off when I’m planning a first date with a man–when he plans absolutely nothing for us to do and when he’s too rigid about an itinerary.
Here’s the thing. I get that these sound like contradicting statements.
But really, what it comes down to is investing time and thought into the two of you having the best time possible.
You want the woman you’re taking on a first date to feel like you’re putting in effort, but not making decisions for her.
When men are too rigid about plans, I assume they’re controlling and a little too old school for my taste.
On the opposite end of the spectrum, being lazy and making zero plans is not the same as being accommodating.
Don’t say to a woman, “I’ll do whatever you want to do!” Women don’t want to date the human equivalent of the shrug emoji.
Try this instead:
“I would love to take you out on Friday night. I know this great place for [insert food you already know she likes]. Want to meet there at 8?”
“Since we’re planning on doing lunch on Sunday, I was thinking about some places in [X neighborhood we’ve talked about wanting to explore together] that we could try. Here’s what I came up with…”
See how both of these examples show effort and initiative but aren’t giving like, toxic Mad Men vibes?
That’s what you’re going for.
2. Have a few go-to first date options ready
Want to cut down on first date stress? It helps to have a few go-to first date ideas in your back pocket.
I hate when I’m out with a guy, and he’s picked a restaurant but didn’t realize it’s cash only. Or he hasn’t thought of a place nearby to go for a drink while we wait for a table.
Especially when you’re in a season of meeting new people and going on a lot of dates, having pre-fab date ideas helps conserve mental energy you need to make sparkling and witty conversation!
Come up with a few restaurants that you know have comfortable seating. Make a list of parks you know that have public bathrooms and a lax policy on smuggling in wine. Know which museums are accessible by public transportation, or have good parking options.
Having these logistics squared away ahead of time can alleviate a ton of awkwardness and stress on a date.
Pssst, this also applies to having a few go-to first date outfits that you feel confident wearing.
For help with that, sign up for a Wardrobe Refresh with me!
3. Be transparent about what you’re looking for
You don’t need to tell a woman everything you’re looking for in a relationship before a first date, but the big deal breakers should be out there like neon signs.
If you are only looking for something casual, she deserves to know this.
And since this is 2022, let me say as well: if you are married, or otherwise in a relationship that is open or poly: you need to share this before you go on a date with a woman.
There’s no shame in the casual game (lord knows I have enough of it under my belt to last a lifetime), but be upfront about what you’re looking for.
This way, you’re laying a great foundation for a first date.
Why? Because you’re coming from a place of honesty and mutual understanding about what you’re both doing there.
4. Text, but not too much
Texting before a first date can feel tricky.
You might be wondering how much to text her, and how to flirt with a girl over text in a way that comes across as enticing but not sleazy.
It’s good to be aware of this. Knowing what to say to a girl over text is a really critical part of making a good impression!
Especially if you want to get a little flirty, romantic, or even sexy.
There are a few things to keep in mind that pretty much give every woman the ick: things like, sending “Good morning!” texts, or an excessive use of emojis and gifs.
I’m not saying to never do these things, but use your common sense.
Do you have a funny meme to show her, or an update on the show you’re both binging? Totally fair game to text her in the morning and be like “Morning! Are you caught up on [X show] because I watched last night and holy shit what an episode.”
This is very different from just a random “Good morning :)” text which, honestly? Just don’t.
Same with emojis.
A well-placed emoji can be a great way to add a little emotion to a conversation and it can be super endearing and wholesome, but going overboard with a million kissy faces and gifs from The Office is a really easy and quick way to turn a woman off.
A note on sexting
Exchanging sexy texts before a first date is a deeply personal topic – I have friends who would never sext with a guy and others who do it regularly.
I’m part of the latter camp and I usually engage in a little racy texting with a guy before a first date, depending on how we’ve met, how long we’re talking before we meet up, and just the general vibe.
I’m a firm believer in collecting as much intel as humanly possible before a date and sexual compatibility is important to me, and I’ve weeded out some very incompatible suitors this way!
5. Keep up the banter
Leading up to a date, I like to hear from a guy daily or every other day.
It doesn’t need to be all day-everyday, but I like to know, especially in this modern age of technology where so many of our interactions are fleeting, that someone is thinking about me.
And this might just be me, but I like to hop on the phone, or FaceTime at least once before an in-person date – it alleviates some of the first date mystery to hear someone’s voice or see a man’s face, and as a safety thing, it helps me feel comfortable knowing the person I’m talking to is who they say they are.
Now lots of people hate talking on the phone and I totally get this and you should never call or FaceTime a person unannounced before it’s been established they’re ok with that.
So a simple, “Hey can I give you a call before our date to chat,” or “Would you like to talk on Facetime or the phone before we meet up?” would suffice if you want to put that move into play but if she begs off, just accept that and keep it moving.
6. Confirm the date
When it comes to confirming the date, you want to make sure she knows your plans are confirmed and that she can rely on working her schedule around them.
I want to hear from the guy the day prior to our date, and again that day.
Our time is precious and you should show her you respect that.
Personally, I like to go to bed knowing in my head roughly what my plan for the next day is – especially if a first date is on the itinerary.
For women, first date prep can mean a lot of things!
While some of us can throw on a little tinted sunscreen and head out the door, others of us (me. I’m us.) like to shave every inch of our body, paint our nails, and pace around our rooms for four hours picking the perfect outfit.
It’s critical I can do all this knowing it will not be in vain.
On the day of, I like to get a text in the late morning or early afternoon confirming our date, and letting me know that you’re looking forward to seeing me.
It’s not like I need you to be texting me all day, but it feels kind of weird to just have radio silence until we leave our respective locations to meet up.
On a first date
1. Show up early
I absolutely despise showing up to a date and waiting for him to get there. If you’re going to be late for any reason (you shouldn’t be, but..) text her with your ETA before you actually are late.
So for example, if you’re meeting for drinks at 7 and you won’t be there til 7:15 because you’re stuck in traffic – text her or call her as soon as you realize you’ll be late, not at 7 or later.
This shows you respect my time – we can’t all control the weather or the traffic and sometimes no matter how hard we try we run late for things, but your date’s time is as valuable as yours, so make sure if you’re late that you’re honest (and apologetic!) about why.
On that note – if you do, for whatever reason, have to cancel a first date – your text should, without question, include specific plans for a raincheck.
Presuming you’ve confirmed the date the night before, and something has come up on the day of, you should text her as early as humanly possible.
If you cancel on me once I’ve started putting my makeup on and getting ready for example, chances are you are not getting another crack at a first date unless you have a REALLY valid excuse.
Being tired from work or stressed because your boss is riding you, are not valid excuses. Things like a flare up of a disability or chronic illness or a family emergency are.
2. Be proactive about her needs
Apply the same principles as earlier to the actual date itself – don’t order for her, but if you need water or napkins or a drink refill, then go ahead and order some more for the table.
Don’t assume she wants another drink, but if she mentions she does, call the waiter over for her.
When the waiter comes to take her order, offer for her to go first. If your food comes before hers, wait for hers to arrive to eat.
All of these rules apply to non-dinner dates too. If you’re going to a museum, ask her what her favorite kind of art is and find it on the map.
If you’re going to see a movie together, suggest a few options and make sure to snag the snacks for the both of you so she can have time to pee before you go into the theater.
You might be like, hey, these don’t really sound like grand gestures but here’s the thing: being a woman means doing a lot of emotional labor.
Most of us are in house therapists for our friends, family, and ourselves – we spend so much time decorating and picking out clothing and figuring out what to eat and a date should feel like a nice little vacation from the amount of self reliance and work that goes into existing.
So doing little things like asking us if we want to split a bag of M&M’s and letting us choose between peanut butter and plain, instead of making us pick the candy for the movie? That’s appreciated!
3. Mind your manners
Not a particularly radical or unique rule but true nonetheless.
The way you treat service works speaks volumes about you to a woman.
I notice immediately how the man I’m on a first date with interacts with the waiter at the restaurant, or the person who sells tickets at the museum, or the bookstore clerk.
If a man doesn’t have good manners with the people who we interact with on a date – especially service workers – it’s an immediate dealbreaker for me.
Personally, this extends to how he tips – I expect a man to tip 20% at a restaurant anytime we go out.
Granted, you don’t always get the chance to peak at the bill on a first date if he’s paying with a credit card (though that has not stopped me from reading entire receipts upside down), but if you continue to date, she will eventually find out what kind of tipper you are, so keep that in mind.
4. Barring unique circumstances, pay the bill
Which brings us to the next tip: pay the bill.
Now, I went to college in the age of the girlboss which means I spent (wasted) probably hundreds of dollars splitting the bill on all sorts of dates, all in the name of feminism.
Now, I’m 29 and truth be told I do not even look up when that bill hits the table.
Typically, if a woman wants to split the bill – she’ll say so.
If money doesn’t come up? Pay it.
Don’t ask if she’d like to split it. Don’t offer to pay it. Just Pay. The. Bill.
Paying the bill, in my opinion, is sort of like opening the door for a woman.
Sure, the implication 75 years ago might have been that women were frail and helpless and couldn’t open their own doors or pay for their own meals and these might have been moves executed as a show of dominance.
But in the year of our lord 2022, when you do these gestures, women recognize that you’re doing it out of respect.
Because you’re a gentleman and because you want to put in that little extra effort to show us you care.
Again, this applies to all sorts of dates – pay for the movie tickets, pay for the concert tickets, pay for the Uber. Just pay for it.
And before you come for me, let me remind you: if you’re doing things right, you planned this date so you’re in control of choosing a restaurant you can afford, or opting for the matinee movie, or the museum when it’s free admission, even.
I’d much rather a guy pick up the tab at a pizza joint than take me out to a fancy restaurant just for show, and then split the bill.
And if you’re on a budget, plan the date around that!
I have fond memories of a man who took me to the local supermarket, where we each picked something for the other to try, then found a bench outside to sit and snack and chat.
Bottom line? There are plenty of ways to foot the bill without breaking the bank.
After a date
1. Let her take the lead
Though we no longer stan John Mulaney (we’re firmly Team Anna-Marie Tendler in this house), the comedian has a great joke about the risks of going to a second location.
And it’s true that if you’ve been kidnapped, the farther you get, you’re basically signing your death certificate.
This is how dating can feel when you’re a woman.
I’ve been on first dates where I would literally walk blindfolded into traffic before I trusted a man enough to be alone with him.
…And I’ve gone on full-on vacations with men as our first date so, truly there is no perfect rule for this one except one: let her take the lead.
If a guy asks me directly on a first date if I’d like to go back to his, it’s an immediate no for me.
The decision to have sex on a first date, or go back to a guy’s apartment for a nightcap and tonsil hockey, is something every woman gets to decide on a case-by-case basis.
The assumption that I’d feel safe doing that says so much about your lack of awareness of what dating is like for women.
But after a great meal filled with flirting and strategically placed touches of each others thighs under the table, I have been known to ask a man what he wants to do next, and say something to the effect of “I’d be up to just go back to mine/yours/the hotel etc.”
If you’re game and want to take her up on the offer, apply all the rules we’ve laid out above – lead with respect and kindness.
When it comes to taking initiative, do so as you ask for consent.
Ask if it’s ok if you kiss her, or take her top off, or if she’s comfortable with you staying over. This way, she’s still in the driver’s seat.
2. Text her after, always
Most women I know pay as close attention to how men communicate post-date, as during it.
Why? Because history shows us that it’s at this point that many guys really show their true character.
Were they being genuine when they expressed interest on the date? Were they in it to get laid?
As for when the post-date text should come, men and women alike debate this question.
Is the night of the date too soon? (No) Is two days later too late? (Yes)
I personally am pretty chatty and also a Leo, so it’s never too soon for me to hear that you’ve had a good time.
I also think it’s really cute when a guy texts me the same night to be like, Hey I had an amazing time and I can’t wait to see you again.
But a text on the following day is also absolutely acceptable, so long as it’s before, let’s say, 6pm.
If you haven’t sent a sexy text before your date but think now might be a good time to open up that lane, apply the same rules as above – be respectful, don’t be demanding, and go with consent not presumption.
I’m not saying you can’t open that door – I love a flirty compliment about an outfit I’m wearing – but let her walk through it.
When it comes to sending pictures – do not send anything unsolicited – ask before you send any lewd photos and wait to get explicit consent.
Also, this might be me, but especially early on I hate when men put in requests – do not start any texts with “Can I see..” unless your partner has given you the green light that she’s comfortable with you asking for bespoke nudes.
If you were intimate on your first date, this can be a great way to open up that conversation too – a simple “I can’t stop thinking about when you [X]” always makes me weak in the knees, or “I can’t wait to [Y] again,” also does the trick.
But be mindful of when you’re sending these texts!
As in, Monday morning at 10am when she has barely answered any emails and is trying to make sense of her to-do list for the week is not an ideal time, but also don’t exclusively text her late at night – this without question gives booty call vibes.
3. Follow the “campsite rule”
Savage Love podcast host Dan Savage talks often about the “campsite rule” when it comes to dating and relationships.
Namely, you should leave the other person in at least as good of shape as you found them.
So, if you decide you don’t want to go on a second date, let that person know.
“Hey, it was great meeting you. I didn’t necessarily feel a spark, but [something you learned about her during your date: ace your bar exam! break your marathon PR! etc]”
Truly, a woman would rather be left for dead than left on read.
And if you do want to see her again? Don’t play games! Be direct and let her know you’re into her. You don’t have to overdo it, but life is hard enough. Why make her wonder if you like her?
Now that you’ve got these first date tips for men under your belt, go forth and get your lovin’ on!