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Best Ideas to Help Guarantee a Great First Date

An Idiot-Proof Guide to Pulling Off an Epic First Date

December 10, 2023

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First dates can definitely be a bit stressful. You’re most likely meeting someone for the first time, and you have a small opportunity to impress them enough that they fall completely head over heels in love with you — or at least, they say yes to going out again.

Adding in the overwhelming fear of being alone and the impact of a constantly changing, digital-based online dating culture means actually meeting can become quite confusing faster than a swipe left or right.

To help you get through those first-date jitters, AskMen has put together this handy, all-in-one date guide. While we can’t guarantee that things will be 100% perfect, at least you’ll know what you’re doing, and that boost of confidence we provide will be the much-needed assist in making it a great first date.

What to Do on a First Date
How to Prepare for a First Date
What to Wear on a First Date
What to Talk About on a First Date
What to Avoid Talking About on a First Date
How to Tell If a First Date Is Going Well or Not
Who Should Pay for the First Date?
How to Follow Up After the First Date

What to Do on a First Date

At some point, a decision will have to be made about what the date’s going to entail. If that’s on you — and as a guy, it often is — you might be wondering what exactly to do.

In natural for people to think the average date is often just two people meeting at a bar for drinks. That kind of stripped-down plan has become popular in the context of online dating-based hookup culture — it’s cheap, easy, and given the way alcohol lowers inhibitions, means things getting physical or sexual at the end of the evening is a bit more likely.

However, if you’re not looking for sex on the first date, or you’re not trying to imply that you are, a bar might not be the way to go. As well, you or your date might not drink, which is as good a reason as any not to patronize a bar.

In that case, what kind of date should you suggest? The best advice, according to Tina B. Tessina, psychotherapist and author of Dr. Romance's Guide to Finding Love Today, is to tailor the plans to something your date actually enjoys.

“If you know anything about them, suggest you do something they’re interested in,” she says. “If you don’t know anything about them, have a few different ideas and give her a choice. Do something light and easy, like a walk in a pretty place or just coffee in a nice café. The point is to get a chance to talk, and to leave it a little open-ended so you can spend more time if it’s going well, or cut it short if it’s not.”

On the other hand, there can be value to a more active date that’s lower on conversation, particularly if you and/or your date are doers more than talkers.

“Offering to take a common interest based activity date is a great replacement than typical drinks,” explains celebrity matchmaker and online dating expert Carmelia Ray. “Activity dates help to break the ice with activities to avoid potential awkward silent moments.”

If your date is the type who wants something special or turns down an initial suggestion for a more traditional evening, dating coach and “Man Whisperer” podcast host Laurel House has several ideas for unique first date ideas. For starters, she suggests splitting the traditional dinner date into a scavenger hunt of sorts by having each course at a different establishment.

“It’s best to find a street known for awesome places to drink and eat, then make a plan to move the party from place to place for a multi-course, multi-restaurant meal,” she says. “The movement makes the date more exciting, allows for different environments — which contribute to conversation, and extend the amount of time that you get to spend together.”

If the two of you are athletically inclined, you could consider working that spirit into the date, too.

“Create a little friendly competition,” adds House. “It’s been shown that people who work out together feel more chemistry towards each other thanks to the release of sweat-induced endorphins. Go play pool, ping pong, or challenge your date to a game of shuffleboard. Once you work up a sweat, grab a drink and dinner and deepen the relationship with great conversation.”

Prefer art to sports? There’s plenty of date possibilities there.

“Get your creative juices flowing together by going to a studio where you get to paint your own ceramics,” she suggests. “Not only is it fun, but you have something to remember the date later.”

She also suggests “working with a canvas and painter’s palette while creating your masterpieces side by side with drinks in hand at a “Paint and Sip” class. (Make sure to call ahead to check on the alcohol situation. It might be BYOB).”

Or, if you’re more literary-minded than visual-artsy, work a trip to a local bookseller into the date.

“Books can say a lot about a person,” notes House. “Pick a cool, funky, independent bookstore and walk the aisles together, each picking out your favorite book and a book you’ve wanted to read, then tell each other about it.”

How to Prepare for a First Date

An amazing first date begins with your pre-date preparations.

“If you know anything about your date, read up on them,” says Tessina. “Ten minutes research on the internet can give you a lot of info for conversation; but keep it general, don’t sound like you stalked them. Remember they don’t know you, and they’re probably going to be nervous too, so you should be as calm as you can.”

In addition to having a tiny bit of background knowledge — if you don’t have access to any social media profiles they have, consider asking a mutual friend about their interests — a good pre-date habit to get into is confirming the date, so you don’t end up with crossed wires where one of you bails at the last minute, or you end up in different locations.

“Text your date the day before or the morning of the date to confirm the time and place,” suggests House. “Aside from that, don’t text, or keep it at a minimum.”

That advice might not apply quite as much if you’ve already developed a serious text-chemistry that’s made a certain back-and-forth normal for the two of you. But if you’re relative strangers, overwhelming your date in the lead-up to the actual meeting could be a definite mistake. If you’re feeling nervous, instead of reaching out to your date for reassurance, try to relax in other ways.

“It's always great to have an opportunity to relax and get into a positive headspace before your date,” suggests Ray. “If you have time to go to the gym, do an activity, hot yoga or some form of exercise, it will help to boost your mood, increase your blood flow and stimulate endorphins in your body.”

What to Wear on a First Date

They say that the clothes make the man, and whatever you think of that, there’s at least a grain of truth to the notion that people see you differently based on how you dress. The same guy walking into a first date with a suit on communicates a very different person than if he were to walk in wearing shorts and a T-shirt.

So how should you dress on your first date? If you care how your date thinks about you at all, the question is one you should consider earlier on than say, five minutes before running out the door. “Planning your date outfit is important for building confidence and making the right impression on your date,” notes Ray. “You should dress to impress and for the date occasion. You don't want to overdress or underdress, or you'll risk being worried and distracted about what you look like on the date.”

Tessina adds that it’s best to “dress appropriately for what you’re doing,” suggesting you “look good, [and] be casual but not sloppy.” And if you’re on a date with a woman, she suggests a novel suggestion — asking other women for fashion advice. “Ask your mom or your sister for advice, if you can,” she says. “She’ll understand what a woman is looking for. Or ask the best-dresser among your friends for advice.”

According to dating coach Connell Barrett, “you can’t go wrong with dark denim, a pair of nice leather shoes or stylish sneakers, and either a button-down shirt or a dressy tee shirt.”

Ray echoes the importance of well-fitting clothing, too.

“No matter what a man chooses to wear on a first date, the first rule of thumb is that it's clean, well-fitted for his body type, wrinkle-free and coordinated,” she says. “Always have a ‘dress to impress’ mindset, because you only get one chance to make a first impression.”

And for those wondering whether it’s worth the effort to dress up a little, Barrett has this advice: “The benefit of dressing well is two-fold: You look more attractive to your date, but you also feel more confident, and that makes you even more attractive.”

What to Talk About on a First Date

Ideally, conversation just flows between the two of you. Whatever you’re doing, and regardless of whether you’re drinking things that’ll help you loosen up (booze, coffee, etc.), you’ll just click without there being a single awkward silence.

Reality, however, can be much different. And while it might be tempting to just say to yourself, “An awkward pause! We’ll never be together!” the truth is that you might not be seeing the best version of the other person, and they might not be seeing the best version of you.

Similar to how some job interview jitters can hinder a perfectly qualified candidate from getting a position, first date jitters can easily make you come off worse than you actually are when it comes to chatting. If that’s the case for you, it doesn’t hurt to have some things to talk about in your back pocket lest a dreaded awkward pause arise.

“This is why you do some research before the date,” says Tessina. “Read their bio if you met them on a dating site. Ask them about their interests. Ask what they like to do, and if you like anything similar, say so. Ask them if they’ve seen the latest new movie, or the most popular show on Netflix or Amazon. Ask them what they like about the town or city you both live in. When they tell you something about themselves, tell them something similar about yourself.”

House advocates for doing a little storytelling to complement asking your date questions.

“Tell stories. That’s what conversation is — stories. Within those stories you can reveal anything about yourself, including the most important topics that have shaped who you are, affect your daily life, and show what you are looking for moving forward — where you were, where you are, where you’re going,” she says. “Think about the story starters that you can build out into more expansive, deeper, more focused conversations to reveal more detailed personality, lifestyle, priorities, and values of you and them. Explain your ‘why’ behind what you do and the life you live, and ask them about their ‘why’ too.”

Looking for some concrete topics to memorize? Ray suggests leaning positive and bringing up things that your date feels good about.

“Great topics include anything where a conversation or story can be shared,” she says. She suggests ones like:

“Tell me about your most memorable vacation.”
“What is your favourite dish and when is the last time you had it?”
“What's your greatest accomplishment and what did it take to get there?”

“Conversation about things that make people happy, such as career goals, fond memories, travel or food are light, easy topics,” Ray concludes.

What to Avoid Talking About on a First Date

While we’ve covered the more obvious things to talk about, what about no-go conversational areas? Sometimes, it’s best to avoid discussing potentially thorny areas like religion or politics, where people often have long-standing and strongly held beliefs.

You should avoid any topics that could lead to debate or controversy such as politics, religious preferences or past break-ups and ex partners,” says Ray. “You should also avoid discussing sex or sexual content on a first date, as that could make certain people uncomfortable if they’re not prepared or open about this kind of discussion on Date 1.”

Tessina agrees that sex talk on a first date is a big no-no, particularly if you’re a guy on a date with a woman, since this could make you come across as lecherous, crude or only interested in one thing.

“Don’t talk about [sex] at all unless she does first,” she advises. “Don’t talk about how much you make, or brag about yourself. Don’t talk too much about yourself. What’s more important is that the conversation go back and forth, and that you get to know about her.”

Not everyone agrees that politics and religion are off-limits, however. House thinks it’s fair game to get into them, so long as the conversation doesn’t begin and end there.

“Talk about everything,” she says. “As long as you don’t talk only about that one thing. It’s OK to talk about politics, religion, your kids, your ex, your dating purpose … It’s important to talk about anything that’s important to you, because you want to learn their perspective and figure out if they are a fit for you so that you don’t waste any more of your time on future dates if you are definitely not good for each other.”

RELATED: Worst First-Date Scenarios

Barrett, meanwhile, believes the main thing to avoid is being negative. If you can talk about tricky issues without making your date feel concerned or down, then go for it.

“A first date is about one thing: personal connection. It’s about how you and your date feel about each other,” he says. “So, you can talk about anything — even politics, religion, and your exes — as long as you’re always filtering it in a personal way. The one big thing you want to avoid on a first date is negativity. A first date should be light, fun, enjoyable. If you just got laid off, or if your dog just died, that’s awful — but you don’t want to bring that kind of negative energy to a date. One simple rule: Keep things positive!”

How to Tell If a First Date Is Going Well or Not

Depending on what type of date you’re on, and how well the two of you are vibing, you might not have a moment to spare when it comes to figuring out how it’s going.

If you’re at a bar, a restaurant or some kind of setting where your date excuses themselves to the bathroom at some point, you’ll probably get a few moments to do a mid-date assessment of how things are actually progressing. If it’s a blast, congrats! And if it’s an absolute disaster, this might be a decent opportunity to suggest cutting it short.

“There are some obvious signs a first date is going well, like flirtatious behavior, great eye contact, lots of laughter and easy conversation flow,” says Ray. “There are also some obvious signs a date is going poorly, such as a lot of awkward silence, little to no eye contact, closed off body language (arms crossed or head down) or vocal cues like sighing, huffing or aggressive behavior.”

Tessina agrees that a smooth and easy conversation is the primary sign that a date’s going well.

“Are they interested in what you’re saying, or is their attention wandering? Is the conversation going smoothly back and forth? Is the time passing quickly? Are you finding things in common? If these things are happening, the date is going well,” she says. “If the conversation is awkward and stilted, you can’t keep their attention, or the time is dragging; things are going badly, and you probably should just end the date.”

House notes that if your date is physically affectionate — leaning in close to you, touching your arm or leg, for instance — that’s often a very good sign as it indicates that they’re comfortable with you from a physical standpoint and there’s a decent that’s paired with a sense of physical attraction. That being said, you shouldn’t assume that things will necessarily progress down that route just because your date puts their hand on your arm. That might be as far as they’re willing to go on the first date.

Who Should Pay for the First Date?

The subject of who pays on a first date is one that’s been well-debated over, especially as changing social mores, the normalization of queer dating and shifting socioeconomic factors have chipped away at the 20th century notion that a man should always pay.

So, with the shift in society, in short: Who pays?

“As a professional matchmaker, my experience has been that most men and almost all the ladies I've matched have an expectation that the man pays on a first date,” says Ray. “Having said that, if you're on a budget, don't feel the need to go to a five-star restaurant on a first date. If a woman feels like paying on a first date, she would be the one inviting the man to a date and making it very clear that it’s her treat. Usually whenever a woman pays, it's discussed in advance about going dutch or that she's offered.”

Tessina advocates for a mix of old-school values and modern-day flexibility.

“You need to find out how she feels about it,” she explains. “If you invited her out, that would usually mean you pay. Some women like it when men pay; others feel you’re trying to buy them. Your best bet is to offer to pay, but don’t insist on it. If she wants to share the bill, agree to it. Don’t take offense either way. You are just getting to know each other, you’ll sort it out later.”

If you do pay, though, remember what it means, and what it doesn’t. You paid for your date’s dinner, which is a polite gesture. It doesn’t mean that you’re going to get some sort of physical intimacy out of it in return. Sex isn’t transactional and can’t be “owed” to someone — only given freely with consent.

“Just because you are paying,” says House, “doesn’t mean that she owes you anything more than eye contact, smile, and ‘thank you so much for dinner.’”

How to Follow Up After the First Date

So, you did it. The first date is over and done with. There are a few different ways to tell whether a date went well or not, but when it goes really well, you typically don’t need a lot of advice.

Maybe a goodnight kiss turned into something more, maybe the date lasted 19 hours, or maybe you drove to Las Vegas and got hitched. Regardless, if the date went well enough to (in your mind) warrant a second date, but not so well that you’re confident about how to set it up, well, keep reading.

“A follow up could begin as early as asking your date to text or call you when they get home to make sure they've arrived safely,” says Ray. “It could also be a good night or good morning text the next day. Depending on the success of your first date, you would know if you should follow up, or if it's best to part forever after your first date.”

And what does that kind of good morning text look like exactly? No need to turn it into something complicated, according to House. She suggests being courteous and referencing something the two of you had discussed on the date:

Thank you so much for dinner last night! I loved hearing about your trip to Cuba. Definitely even more a bucket list for me now. I look forward to seeing you again soon.

If you felt the date was a flop, House suggests something polite, but clearly indicating you’re not interested so you’re not in danger of leading them on:

Thank you so much for dinner last night. It was really nice to meet you. You seem like such a good person, I just don’t feel like we are a match/looking for the same thing.

Whatever you do, dragging things out and giving them the silent treatment is a bad move. That might have been good dating advice in decades past, but in our modern, immediacy-focused digital culture, spending days without reaching out first and foremost communicates that you don’t care about the other person.

“If you had a good time and want to see that person again, do not ‘play it cool’ and wait two or three days to text or message them,” says Barrett. “That comes across as disinterested at best, and manipulative at worst. Be real. Put yourself out there. Send a short, playful, sincere message saying that you had a good time and would like to see them again.”

If you’re worried that’ll make you seem overly desperate, you should remember that dating culture — like societal conceptions of masculinity general — is in flux, and generally, people are becoming more accepting of men who are open about their feelings rather than closed-off and stoic.

RELATED: Second-Date Tips for Success

“Most men are afraid to show how they feel, for fear of looking weak,” Barrett says. “But it’s actually very attractive to be vulnerable. And it also feels good to be honest and authentic, rather than feeling you have to play games.”

First dates can be stressful, but they don't have to be. If you go in with the right attitude and a little bit of forethought, you can significantly increase the likelihood that you (and your date) will both have a good time. Even if they don't turn out to be the love of your life, having fun is never a bad thing.

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