Together Or Separate? How To Respond To This First Date Question!

First, second, and even third dates can be made awkward for a variety of different reasons but lately the question of “who pays the bill?” has been the topic of conversation among my single friends, men and women alike.

I caught up with a friend over coffee and she confessed she was back in the singles pool and actively dating again.

Exciting? Very. Awkward? Extremely.

Gabbing about our latest dating experiences, my witty, outgoing, gorgeous friend surprised me when she admitted she was at a loss for words on her last date. She said,

“The date was going great, both of us in the groove, conversation flowing, but then my anxiety crept up at the very end when the waiter looked down at the two of us and asked, “will this be together or separate?” I froze instantly. So many thoughts whirling in my mind…Do I grab my wallet? What if he puts his card down first, do I put mine on top? Do I argue with him? When do I stop arguing with him? Do I offer to pay half? Do I sit and say nothing? I got so awkward! I didn’t want him to think I was expecting him to pay the full bill!”

My friend went on to tell me she has gone as far as buying gift cards to restaurants for dates, telling her date it was a present from a friend, just to avoid the awkward method of payment at the end. This way they were “both” getting treated…

I realized quickly this was a problem for my friend and most likely other singles attempting to navigate the uncharted realms of the dating world.

Expectations can vary among daters, but I have always stuck to a couple guidelines before heading on a date to keep me in check.

Never assume the bill will be covered

The majority of first dates I have been on, my date has covered the bill but this isn’t always the case. Whether it be drinks, dinner or a movie, I have never expected my date to pay the full bill. When the check is placed on the table, pull out your wallet. If your date says they’ve got this one, thank them politely, put your wallet away and say you’ve got the next one, if you want a second date that is.

Always carry cash

Take money out prior to a date just in case you two decide to split the bill. If your date only has card, let them know you have cash and have no problem going halfsies! Cash in your wallet is also helpful at old school restaurants that refuse to take card! I have definitely found myself in that awkward situation before.

Talk about it

I would reserve this conversation for the fourth, fifth or sixth date when you have established some sort of exclusivity. I think it is really important to understand each other’s expectations and dating style early on. The rule that has worked best for me in the past is going date for date. For example, if I treat my boyfriend to a date night on Friday, he will get the next one the following weekend, so it becomes an equal playing field.

I want to know how you choose to pay the bill?! Together or separate?


5 First Date Ice Breakers

Palms are sweaty, knees weak arms are heavy…as you take one final look in the mirror before heading to your first date with a new potential love interest. On the way to your date, you start running through a long list of questions as though you are about to conduct the most important interview of your life, tempted to ask the cab driver if he/she approves. You get a guttural pang of anxiety as you step toward your date and take one last moment to pray to cupid that it goes well….

If you get the first date jitters, this one is for you! Sit back and relax as I take you through the top 5 first date ice breakers that can help ease your nerves.

  1. Activity vs. The Interview

No one wants to sit across the table from a drill sergeant and be hammered with questions like “where do you see yourself in 5 years…or “how many kids do you want to have?” This is not an interview! A great way to switch things up on the first date is by planning an activity together. No, I don’t mean going to a movie where you sit in silence…I am talking about a hike, bowling or pizza making. Through these fun and flirty activities, you can engage and interact with one another without playing 21 questions.

  1. What do you like to do for fun vs. What do you do for work?

Let’s skip the routine question of “what do you do for work?” Yes, you may be curious but try your best to avoid this one on the first date and instead ask “what do you like to do for fun?” Who wants to talk about work after just completing an 8 hour shift? By asking someone what they like to do for fun, you are asking them a more personal question in which you will most likely receive a more elaborate answer. Following this question, you have a better chance of finding out common interests.

  1. Pick up lines vs. Sincerity

“If you were a vegetable…you’d be cutecumber…” “You must be a keyboard because you’re just my type…” If you have thought about using these or have ever used them in the past, please stop and drop the lines immediately. Compliments are important to give to a first date but make it sincere. There is a huge difference between simply saying “you’re hot” and “I am having a really great time with you.” The later will resonate with your date as it has more substance behind the words.

  1. Smile vs. Resting B*tch Face

A smile goes a long way! Seriously, lets show off those pearly whites like you’re auditioning for a Colgate commercial. Definition of the resting b*tch face for those of you new to this slang; a person, usually a girl, who naturally looks mean when her face is expressionless, without meaning to. Starting the date off with a cheerful introduction will immediately break the ice for the two of you.

  1. Short & Sweet vs. The Neverending Story

It’s the Neverending Story…the date that just drags on a touch too long. Everything was fantastic for the first two hours but all you can think about now is getting home, slipping on your onesie and turning on OWN network as you devour a bag of salt and vinegar chips. Your very first date should always be short and sweet leaving you each wanting more and a second date. In other words, leave them with a taste, not the full meal.

So there you have it! Take a deep breath,  get out there and use those ice breakers!