Business Travel Just for Fun

Swipe Right: Eight Awkward Moments in a First Client Dinner and First Date

You’re at the dinner table, fumbling with your phone and waiting for the other person to arrive. You’ve never met them in person but you know what they look like from their social media profile and you’ve communicated a bit on the phone. Your palms are sweaty and you’re feeling nauseated, hoping this night doesn’t turn out to be a disaster. When the person arrives, you take a deep breath, stand up and hold out your hand for the very first in-person introduction, all while hoping they don’t notice the look of terror on your face. You know exactly what we’re talking about, of course – the first dinner you have with a new client prospect.

Oops, did you think we were talking about something else? A first date, perhaps? It may seem like an odd correlation but the awkward happenings that occur on a first date are quite similar to those occurrences during a first client dinner. And since this is the season of love, we thought it’d be fun to see how well our love advice relates with our work advice. So, let’s break it down – here are eight awkward moments during a first client dinner and first date, and our tips to stop the awkwardness:


Awkward Moment #1: You don’t know where to go

Things get nerve-wracking from the moment you need to plan the soiree. What if you take your client to a fancy white tablecloth restaurant, only to find that they’d rather talk business over darts? Or, what if you suggest to your Tinder match a BBQ joint and they’re vegan? Let us help you plan your evening for each scenario:

First Client Dinner: At Dinova, we make this easy. Our search tools will help you find a place that’s close to your client’s work and easily fits their needs. Do a bit of research and pay attention to the company culture before choosing a place to dine. If it’s a conservative culture, choose a nice restaurant with a well-rounded menu. If it’s an eclectic culture, opt for something with more of a fun, local flare. If you can, ask ahead of time if your client has any dietary preferences – with Dinova you can search for restaurants that cater to specific needs. If you don’t have the chance to do that, opt for places that have gluten free and vegetarian options, as these are commonplace.

First Date: Before your first date you should have gotten to know the person well enough to know what atmosphere they’ll enjoy (and if you haven’t, you may need to rethink this whole plan TBH). If you know that the person has a huge sense of humor, consider a comedy bar. If you know they are very active, suggest a casual diner after a rock climbing session. You can also keep it sweet and simple with a popular bar that you’re both somewhat close to and familiar with. Our big advice for a first date is to not break the bank – a four star, $200-a-plate meal is for an anniversary, not a meetup.

Asian Woman shaking hands for Business at restaurant, Woman working concept.

Awkward Moment #2: You’re not sure what to wear

Impressions matter, and it’s highly unlikely the potential client or potential love of your life fully realizes your fashion sense before the first encounter. The rules are a bit different between a first client dinner and a first date.

First Client Dinner: A professional meal demands a professional look. Even if you think a suit jacket may be too formal, it’s easier to take the jacket off if you are overdressed than to go under-dressed. If you’re planning to head to dinner right after work, make sure you’ve dressed up a bit more formal than usual for the day.

First Date: The dress code is a bit more relaxed here. No matter what, a pair of nice jeans and a button down top will do you just fine. Just make sure everything is clean and not wrinkled – seriously. We can’t tell you how many dates we’ve had who show up looking like they’re waiting for their load at the laundromat!

Iced tea in glass jars

Awkward Moment #3: You need a drink (but you’re not sure if you should)

Bottoms up? Not really. Here’s what you should do:

First Client Dinner: Alcohol is not a good idea, even if you’re meeting up at a place known for cocktails. You’re there for business, not pleasure, and it’s your first time meeting with this potential client. Stick with water or iced tea, and if your client insists, order a glass of wine and limit your intake to half a glass.

First Date: Here you can have a bit more fun – but not too much! On average, you will be drinking on a first date, but it’s polite to see what your date does first. If they order a water, do the same. No matter what, don’t get too sloppy and keep all first dates to a two-drink maximum.


Awkward Moment #4: You need to break the silence – FAST.

Ah, the moment where you hear nothing but glasses clink and waiters hustling and your brain is telling you: Say anything! Literally anything will do! When it comes to breaking the silence, preparation is key.

First Client Dinner: In the beginning you’ll want to connect with your prospective client one-on-one; people want to feel connected, not pitched. Asking thoughtful questions about their job shows your interest and your investment in the company, which will be helpful when you get to the nitty gritty. Prepare questions about how their position has evolved over the years, a specific project they are working on and thoughts on some industry-related news. Knowing this from the get-go will also help you explain how your product or service will help them personally further their position or improve their company overall.

First Date: Just like a first client dinner, people want to feel connected. Ask your date about their family, hobbies, pets and more. Unless you connected because of a common interest related to these topics, stay away from any conversation related to religion or politics. It’s a date, not a debate.

Young woman cutting pizza

Awkward Moment #5: Can you eat without looking like a pig?!

Whether it’s a potential client or potential life partner, your first time eating with them is going to be rough as you’ll suddenly become very aware of every movement your mouth makes as you take a bite. For both scenarios, our advice is the same.

BOTH the First Client Dinner and First Date: Order a menu item that is simple and neat so that you don’t risk any spillage. A salad or chicken plate is perfect, while you may want to hold off on the pasta and sloppy sauces. Even if you’re in a casual setting such as a pizza place or BBQ joint, you can eat cleaner than usual by using utensils and resisting the urge to over-sauce. Another good tip is to have a snack beforehand so you don’t arrive famished; in both scenarios, the conversation is more important than your appetite. Finally, remember all the rules your parents taught you at the table. Eat with your mouth closed and don’t talk with your mouth full.

Businessman swiping credit card

Awkward Moment #6: You don’t know who should pay

The meal is over and the check arrives, but who gets the bill? No matter what, you should always come prepared to pay. The situations between a first client dinner and first date slightly differ, but not as much as you may think.

First Client Dinner: If you were the one who invited someone out, you should plan on paying the check. Let the waiter or waitress know in advance discreetly before you sit down that the check should go to you. If you were the one invited and it may seem a bit unclear, take cues from the host. If after a minute or so they are not reaching for the checkbook, graciously take the bill and oblige.

First Date: Before we continue, understand that we wrote this blog in 2018, not 1957. We are not assuming that the man must pay for the first date nor are we assuming that the date is with a man and a woman. We say that the rules for a first client dinner follow in a first date – if you are the one who invited the other party, you should offer to pay. If your date insists on paying the bill, accept gracefully. Also, be gracious and accept if your date suggests splitting the bill. If the night was a success, you’ll have the opportunity to go all out for that special someone on date #2.

Beautiful african woman using cellphone outdoors

Awkward Moment #7: Things went well but you don’t know how to follow up

The night is over and it was a hit – now what? You may lose sleep tonight wondering how you should follow up and when, but we’re here to help!

First Client Dinner: Send a memorable email within 24 hours to demonstrate that you are thoughtful, reliable and consistent. Show that you listened by sharing a memorable portion of a conversation, such as a new, exciting project for the company. If there was an agreed upon sale or business transaction, include that information in the email as well. Don’t take it personally if you don’t hear from them right away – they are very busy, after all! If you don’t hear back within 48 hours, follow up with a pleasant phone call.

First Date: We’re a bit afraid to tackle this one because everyone seems to have strong opinions on the “rules” – some think you should text three days after the date, others think you should call the day after, etc etc etc. Our thoughts on this controversial topic is that your communication patterns after date #1 should match the way you communicate on a regular basis – these communication patterns become important as you build upon a relationship. Are you a texter? Send a text the next day saying you enjoyed your time and ask when they are available next. Are you more traditional? Call them and suggest an outing for date #2. We know that this moment causes a lot of anxiety, but the sooner you get it over with, the sooner you’ll get to know that special someone better.

Portrait sad business woman typing sms phone street

Finally, Awkward Moment #8: The night didn’t go well and you’re not sure how to follow up

Not everything goes as planned – in professional and personal settings. But that’s okay! Here’s how to handle it:

First Client Dinner: Didn’t get the deal? It’s still important to keep a professional relationship. Send them a follow-up email within 24 hours just like you would in Awkward Moment #7 – thank them for their time, recall a part of the conversation that impacted you and let them know that you wish to keep in touch for future consideration.

First Date: You can wipe the sweat off your brow here, because our advice is simple. If the first date didn’t go well, there’s no need to follow up. It’s likely that you both know it’s not going to work out, so it’s best for the both of you to move on. If they try to contact you, politely inform them that you enjoyed the evening but do not see a future and wish them the best.

What do you think of our awkward business dining mentions, and do you have any tips of your own? Share them in the comments below!


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