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First Date Tips: Relationship & Dating Experts Comment

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First dates can be nerve-racking, but they don’t have to be — and most certainly shouldn’t be. Dates, by their nature, should be fun. To help you try to enjoy and succeed in your first dates, this piece is a compilation of tips and advice from dating coaches, relationship experts and people who have had a great first date on what they feel is the #1 thing people should pay attention to on a first date. Of the 21 comments that have been submitted to us so far (submit a comment here if you have something to add), you’ll notice many have websites in the dating space and are more than qualified to give good, practical advice on dating. I therefore strongly recommend reading through these!

To summarize, here are the main points people have brought up so far (I’ve included links that will bring you to the main comment bringing up each point). There are just 1 or 2 differing opinions about what kind of date is best (such as meeting at a coffee shop or doing an outdoors activity), and we’ll leave it up to you, the reader, to decide what resonates the most with you:

  • Listen to what your date is saying, and try to go a little bit deeper into the why of what they do or what they like (link)
  • Frame the conversation around your dates interest for much more engaging conversation (link)
  • Don’t ask boring questions like “What do you do?” – rather, ask engaging questions that elicit an emotional response (link)
  • Remember of course to wash your hair and brush your teeth (the usual stuff)
  • Pay attention to your body language (link)
  • Don’t give out everything about yourself on the very first date (link)
  • Remember to enjoy yourself (link)
  • Be adaptable (link)
  • Treat everyone around you, and especially anyone serving you (such as waiters if you’re at a restaurant) with respect (link)
  • Never be too pressured to be in a relationship, and be your own person (link)
  • Similarly, be true to yourself and listen to your gut (link)
  • Without being stalkerish, Google the person before the first date and have a quick look at their social media (link)
  • Behave confidently and relaxed, which is made easier if you treat the date like a normal casual outing with an old friend (link)
  • Know what you’re looking for (such as a committed relationship or something casual), and make sure as soon as possible that your date is on the same page (link)
  • Have a personal anecdote to share (link)

Having participated in a lot of dates, before I found my only one beloved, I can confidently say that a girl needs to wash her hair (the same is fair for a boy), do light make-up and put on the most convenient shoes she has. It's ridiculous to watch girls suffer in high heels. I've even seen a girl clinging to a fence so she won't fall off her high heels. The situation got worse because of the very short dress. Don't do that.

One more tip: Listen to the person you're talking to, don't talk about yourself too much. If your partner's interested in you and trying to get to know you, that's a good sign.

--Tatiana Gavrilina, DDI Development

PERMALINK: https://outwittrade.com/first-date-tips#tatiana

Rather of simply wondering what someone is doing for a living or what their favorite movie is, figuring out why they are doing what they are doing or why they like that movie is going to allow them to share something about their personalities and build a deeper connection.

Go to your date armed with some fun ice-breaker conversation, and share stories about yourself. Ideally fascinating or amusing ones! And remember listening to what your date tells you about yourself, really. The conversation will flow more easily and naturally if you really listen, instead of thinking for the next thing to say ahead of yourself.

--Lesley Reynolds, Harley Street Skin Clinic

PERMALINK: https://outwittrade.com/first-date-tips#lesley

1. Bond over a board game

It may sound old-fashioned, but board games are actually fun to bond over and to see how well you work together or against each other. They are intellectually stimulating and a good way to see a person in a competitive environment, with low stakes. Board games also make for good double dates. And they may be played online too.

2. Sip coffee together, by books

It would be just a coffee, but the greater stimulant would be the surroundings (offline, at a bookstore, or virtual) and the conversations that books enable. Walk through sections that interest either or both of you, talk about books – or their movie adaptations – that have influenced you, and read select passages of favorite or random books to each other. You’ll discover quickly whether there can be a true meeting of the minds.

3. Attend a cooking demo

The way to the heart may be through the stomach. Even otherwise, cooking is an intimate exercise and it allows you to see how comfortable you are in each other's space and also how well you might work together. So, sign up for a cooking class, whether offline or online, and cook a meal together.

4. Do good (volunteer) together

Volunteering together is a great experience and a sure way to have a meaningful first date. If there's already a cause or do-good project that's dear to you, your date will get to see you for who you are and you'd also get to gauge how that important part of you would sit with them.

Alternatively, depending on your expertise and availability, look up local organizations and sign up to be a weekend volunteer for a cause of your choice. (And there's no shortage of ways to do good in these trying times.) Inviting a date to join you for such an activity would go a long way to build mutual respect, bond at an emotional level, and lay the foundation for a friendship and more.

5. A walk or ride in a park

Meet at a park or garden in your city. The quiet in the park can be a blissful escape from being cooped up indoors and would let you be fully immersed in getting to know your date. If you can rent bicycles in a large park, spend some time riding and exploring the park together for a memorable, off-beat date experience.

--Anil Kumar, Jodi365.com

PERMALINK: https://outwittrade.com/first-date-tips#anil

Prepare for engaging conversation.

Yes, you read that right. Stop working yourself up into a ball of anxiety over what you’re going to say. Do your research. Find out what your date’s food preferences or hobbies are beforehand and frame questions around those interests.

If you’d rather not spend a good hour or so scrolling through his/her Instagram photos, lead with a topic that you know a lot about.

On my very first date with my now wife, I started with a joke about coffee beans, which she (fortunately) thought was hilarious. It certainly broke the ice and that memorable time lasted until the next day.

--James Kilpatrick, Beanie Coffee

PERMALINK: https://outwittrade.com/first-date-tips#james

The biggest turnoff for me when going on a first date would be bad breath! Therefore, my number #1 tip for people going on a first date is to visit a dentist or hygienist a week before the date and get a thorough round of scaling and polishing. Remove those stubborn coffee stains and the tartar that is causing all the funky smell. However, you would want to avoid doing right before your date because you might end up with bleeding gums and that can be pretty frightful. Do it about a week beforehand so the gums have time to heal and keep it clean within that week. By the time the time comes, you will have fresh, great-smelling breath. With that comes confidence and the conversation will naturally flow!

--Albert Lee, Home Living Lab

PERMALINK: https://outwittrade.com/first-date-tips#albert

Take An Interest And Ask Questions That Elicit A Positive Emotional Response

We have all heard this a million times that being interested in your date makes you interesting but for some it's easier said than done. How do you ask questions that are going to guarantee an interesting conversation? Asking mundane questions like What do you do? Where you are from can lead to mundane answers so look at asking questions like your favorite meal in the world, music, movie and perhaps even find things you mutually hate like a destination you both find overrated. This way you will have a lot to talk about and you won't have to worry about orchestrating the conversation as it will be a lot more seamless.

--Greg Flemming, MintDate.com

PERMALINK: https://outwittrade.com/first-date-tips#greg

Pay Attention to Your Body Language

Nonverbals (body language and facial expressions) are perhaps the loudest thing you communicate. So while on a first date, it’s good to be mindful of how you act and present yourself.

Now, you might ask — how can I be aware of your body language and still act natural? All it takes is catching known negative body language and tweaking it a little.

I used to have this habit of folding my arms and leaning back on my seat while listening to a date talk. I would then get a disapproving look from the person across the table. Those first dates never turned into something more serious until I met my girlfriend. When I did this to her, she actually stopped talking and asked if I was bored. I quickly explained that I wasn’t and she replied by saying that my body language showed otherwise. Fortunately, she let that one slide, and things took a better turn from there on.

If you’re interested in what your date has to say, don’t fold your arms. Tilt your head toward them. Lean in. These are nonverbal indicators showing your date that you like what they have to say and want to hear more.

--James Bullard, Sound Fro

PERMALINK: https://outwittrade.com/first-date-tips#jamesb

Sometimes you feel really comfortable on a first date. I don't mean to be pessimistic but don't get too comfortable- ie give out your last name or business name for example.

I did this and found myself being followed on instagram which wasn't so bad but then comments were sent on pretty much everything I appeared on on social media and I realized he had gone through and read/watched anything with my name on it. While I know I should keep these things private I think that I felt a level of comfort on the first date that was false based on the texting and phone call prior and in reality it takes a long time to get to know someone.

--Margo, KuraDesign

PERMALINK: https://outwittrade.com/first-date-tips#margo

Get out of your head and enjoy yourself. Many people get so caught up in over thinking and over analyzing the date, they forget to have fun! If your date doesn't think you're a fun person to spend time with, they won't want to continue to date you. Stop treating first dates like someone is interviewing for the position of being your boyfriend or girlfriend. Start treating your dates like opportunities to laugh, have great conversation, and enjoy yourself!

--Amber Artis, Select Date Society

PERMALINK: https://outwittrade.com/first-date-tips#amber

Tip #1: Forget about meeting up for coffee, lunch, dinner, or drinks.

Those aren't dates, they are job interviews. Instead, do something where you can stay on your feet. Meet up for a walk at a park, or an area with some shops. Go to the farmer's market on a weekend morning. Go bowling or meet up to shoot pool. Meet at a gallery or museum. Anything where the two of you are moving around and experiencing something together will give you a much better sense of the other person than you'd get from sitting across a table, asking the same 20 questions you've asked on your last 10 first dates.

Tip #2: Be adaptable.

When my wife and I had our first date, we were going to meet up for a traveling Smithsonian exhibit that had come to town. Unfortunately, the website was wrong and the exhibit had left for Malaysia the day before our date. We arrived to an empty warehouse where crime scene tape and body outlines were being set up for their next event - The CSI Experience. Thankfully, there was a mini golf place a few doors down. She kicked my butt, but we had a great time. That was 8-years ago.

--Eric Resnick, ProfileHelper

PERMALINK: https://outwittrade.com/first-date-tips#eric

Give your date an early compliment if you like him/her so you don’t get moved to the friend zone. "That shirt looks great on you. You have such great taste." By complimenting your date right away, it shows you’re interested in him/her.

Believe it or not, you are being judged on your first date with him/her so make sure you treat the servers or anyone not on the date with you with respect. The way you kid around with the server is going to score you points.

It shows your playfulness if you’re a woman and you are kidding with the female server. If you’re a woman and teasing the male server, that might be taken as you flirting with him, so don’t do that!

--May Hui Bugenhagen, Matchmaker May

PERMALINK: https://outwittrade.com/first-date-tips#may

As a single guy, I love and hate first dates equally. They are both exciting and super stressful!

My tip for anyone going on their first date is to listen. The first time you spend one on one with someone whether dinner, drinks, or in another date night setting you want to get to know that person. Try not to talk too much about yourself and remember to ask questions. It's not an interview but after each time you speak about yourself ask them a question.

--Ryan Raffel, PaleoPhysicality

PERMALINK: https://outwittrade.com/first-date-tips#ryan

I've been writing about love and relationships for quite a while now. Through my own personal experience as a 38-year old single man, there's one dating tip I absolutely swear by:

Stop pressuring yourself to be in a relationship.

I think there’s too much societal pressure on single people to change their relationship status. The result of this pressure is that many people end up entering relationships based on expectations that are difficult to live up to.

If you really want to create a genuine, enduring, and healthy relationship with someone, you need to let go of the notion that you need someone else to complete you.

Before you even go on a first date or entertain the notion of finding a life partner, you need to be your own person—someone completely happy and at home with who you are, with or without a partner.

--Justin Brown, Ideapod

PERMALINK: https://outwittrade.com/first-date-tips#justin

I host a relationship podcast and we recently did an episode about how you should always pre-screen people before your first date. Google them, look them up on social media (make sure they're not married or have a criminal record - this happened to me and friends of mine!) and I also suggest talking to them on the phone before the first date - you can get a lot of insight into someone by a simple phone call.

By speaking to someone prior to the first date, you build up a foundation and a sense of familiarity so by the time the first date comes, you'll be more at ease and feel like you already know them.

--Rachel Burke, Relationships, Romance & Propaganda Podcast

PERMALINK: https://outwittrade.com/first-date-tips#rachel

There are many tips for first dates, but the most important one is to simply be true to yourself and to listen to your gut. We all have a subconscious that unfortunately, we ignore far too often. It's been said that within 9 seconds of meeting your date, you determine subconsciously if you are attracted to them, and within 30 seconds, you determine if you will see that person again. Think about it. I bet if you met online and meet for a first coffee date, if you are honest with yourself, you realize there is truth to that! However, when you sit across from your date, the most important thing is to be open to the possibility, yet be completely yourself. It's not fair to anyone to simply tell the person what you think they want to hear, as in the end it will just be a waste of everyone's time. The most important thing is to let them see the real you. Be yourself, in all your quirkiness, beauty and unique individuality. If your date doesn't see how special and unique you are, then they are not for you!

--Trish McDermott, Meetopolis.com

PERMALINK: https://outwittrade.com/first-date-tips#trish

As quarantine is being lifted in most cities, other than the friendly reminder to wear a mask and carry hand sanitizer in your purse, here are some first date tips that every woman should consider.

1 - Own your confidence, not your desperation.

It’s been months since the last time you may have went out on a normal, in person date which is more than enough reason to feel a little desperate but do your best to not come across overly flirtatious, too willing to do anything to get his attention or have him notice you as someone who would be the perfect girlfriend.

Instead behave confidently. Yes, it’s okay to be happy and attentive however, make sure to treat the date as if it’s a normal casual outing with a friend. Relax, let the conversation just flow by itself. The more relaxed you are, you’ll come across as a woman who knows her worth and isn’t trying to get married after the first date.

2 - Don’t have sex, just yet.

No matter what you’ve been told, having sex too early can have an adverse effect on your dating relationship with this person. I don’t like to admit it but reality is, if you sleep with them too soon they will assume that’s what you do every time. This can be a huge turn off. So, when your date makes any kind of sexual advances, respectfully decline letting them know what your expectations are.

3 - Keep certain life events to yourself. They don’t need to know your entire life story.

It may be hard to not be extremely talkative but do your best to keep the conversation light-hearted. No need in spilling all the tea in regards to everything that you’ve ever experienced before meeting them. Remember: the point of the first date is to meet and get to know them over time, not in one night.

--Ro Sanchez, @she.sips on Instagram

PERMALINK: https://outwittrade.com/first-date-tips#ro

So many people go out on dates not knowing entirely what they want and just hoping that the person on the other side of the table will lead them to it. This never works. To have a great first date you have to know exactly what you think makes a great time and a great date.

How do you make this happen? Take charge of your feelings and the situation. If you're honest with yourself and admit that you want a committed relationship, then only go out with people who demonstrate that they want this to. Direct the conversations to topics that cut to the point and ask that person what they want, too. This will help you quickly find out if you're on the same page and compatible with this person.

If you're someone who is just looking for a good time and short term fling by all means go for it. One night stands are fun and carefree, just don't expect a call the next day and don't be disappointed when you don't hear from them.

You're the CEO of your own dating life, so you should call the shots and go after exactly what you want. You also shouldn't tolerate any sloppy interns - even on day one.

--Molly DeMellier, LaunchSquad

PERMALINK: https://outwittrade.com/first-date-tips#molly

On a first date I tell my clients to have a personal anecdote to share. This story should be something that gives your date insight to who you are beneath the surface. I recommend a slightly embarrassing story to help your date put their guard down. Of course it should be a story you are comfortable sharing and that no longer actively causes embarrassment, something that you are now able to look back on and laugh about.

Another tip is to have a first date uniform prepared. This takes all the guesswork and anxiety out of preparing for a first date. Thinking about what to where should be the least of your worries.

--Alexis Germany, AlexisGermany.com

PERMALINK: https://outwittrade.com/first-date-tips#alexis

First dates are really all about getting to know a person you are romantically interested in. If you have been chatting with someone you met on an online dating site or someone your friend introduced you to for some time, the first date will be the stepping stone that will determine whether or not there is actual chemistry and connection- which will then determine what step will be taken next.

For this reason, it is important to ask questions that will help you get to know your date better. Having questions in mind before meeting the actual date in person will not only help you get to know your date better but it will also help the conversations flow. If you are not sure what to ask, it can help to think of what your deal breakers are and take it from there. For example, if religion is important to you, you can ask, how they feel about religion; If education or having a stable career is important to you, then, you can ask about their occupation or if they have any personal development goals; If you simply wish to get to know who they are as a person, then you can ask what their interests are, what hobbies are they into, what kind of music do they like, etc. The point is to have questions in mind that you can ask to get to know your date better.

Being an active listener is also very important on a first date. If you are asking all the right questions but are not giving them your attention, then there is really no point in asking the questions. Being distracted by looking at your phone or at the people that surround you, not only looks bad and rude, but it sends the message that you don't care what they have to say. This is not a good way to start the first date and you can also expect not to have a second date as a result of not giving your full attention.

--Stephania Cruz, Datingpilot

PERMALINK: https://outwittrade.com/first-date-tips#stephania

First dates can be nerve-racking. First dates are where the impressions, pressure, and everything in between is. There’s too much that you think you need to think and plan about. It’s even harder when you’ve prepared so much and found yourself at a loss when you get there. Don’t be like that.. There’s a good way to prepare for a first date to make sure that it doesn’t get as awkward as most dates go.

The #1 tip I always say is to always choose the right date place. This is so important because the location that you choose sets the tone of the date. It would be an easier task if you already know what your date enjoys, so you can bring them to that kind of place. If you don’t know much about them yet, make sure to choose a neutral date place. One that won’t pressure either of you.

It's very important to choose the right place that won’t pressure both of you because first dates are supposed to be fun. The time together should be spent getting to know if the two of you “click”. When you choose a place that can pressure the two of you, it will be hard to withdraw once either of you doesn’t feel comfortable anymore. Instead, opt for a light and casual place like maybe a coffee shop or a local bar. There won’t be too much pressure and the two of you will be more able to talk about anything.

First dates don’t need to have too much pressure and awkwardness in one day. You can turn it around by making wise choices early on. What’s important is you enjoy yourself, and if you’re not enjoying it, don’t be afraid to admit it and leave.

--Sam Whittaker, Boureston Media

PERMALINK: https://outwittrade.com/first-date-tips#sam

Keep it casual.

Inner Circle did a survey recently that revealed it takes the average dater 42 minutes and 29 seconds to decide if they want to see someone again. So a casual, “low-investment” activity like a cup of coffee and a stroll around the neighborhood, or a cocktail at a venue with outdoor seating is perfect.

It’s long enough to make a great first impression, but without the anxiety that often comes with committing to an hours-long dinner+show experience.

The other advantage to a short first date is that you can always extend it if things are going great. Do a little recon first so you’ll have a few ideas in your back pocket. That way, if sparks are flying over cocktails, you’ve already got the perfect spot for tapas in mind.

--Scott Valdez, VIDA

PERMALINK: https://outwittrade.com/first-date-tips#scott

Katie Holmes

I am the lead editor of OutwitTrade and an accomplished writer and internet marketer. These days I spend a lot of my time organizing community discussions here, writing content, and outreaching to different people.

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