To Pay Or Not To Pay…


Melissa writes:  I’m a 33 yr old girl and I date a lot.  I find the whole getting the bill part awkward when out with a guy on a first date.  Do I pay?  Does he pay?  Should I always offer?  I make a lot of money and I feel like sometimes when I’m out with a guy who probably makes less than me that I should pay.  What’s your position on this?  Thanks, Melissa.


Melissa, I’m so glad you asked that question!  In my experience, this very issue has been the deal-breaker on so many occasions, however, the affected party wouldn’t have known that was the reason date number two never materialized.

Here’s my take on the whole thing:  men are as confused as women are, when it comes to the “who pays” dilemma.  Thanks to the feminist movement traditional roles are no longer universally embraced.  There are men who genuinely respect women and, in doing so, do not want to offend their sense of independence by insisting on paying the bill.  Similarly, there are men who use women’s desire for independence as an excuse to avoid having to pay the bill.  There are women (like myself) who, despite being career-oriented and financially independent, would appreciate a man who is happy to pick up the bill, in the name of tradition.  Similarly, there are women who are uncomfortable with a man paying for them, especially on a first date, for any number of reasons.  So, where does that leave us?  

Here are my tips which are meant to apply to men and women alike:

STACIE’S TIP # 1:  Know thyself.

If you are woman and feel better when a man pays for you, acknowledge and embrace that without judgment.  Same rule applies if you are a woman who prefers to pay for herself or a man who prefers to pay/not pay.  The point is – there is no right or wrong.  What is key is that you remain true to yourself while being sincere with the person sitting across from you.

STACIE’S TIP # 2:  Be deliberate in your actions. 

Ladies…how many times have you reached for your wallets to feign interest in splitting the bill only to be secretly furious (or moderately disappointed) when the guy actually accepts your offer?  This is unfair on our part and sends the wrong message – especially when the gesture is insincere and only to give off the appearance of being well-mannered.  Refer back to tip # 1 and then act accordingly.  If you feel strongly that a man should pay on a first date then, when the bill comes, once he realizes that you are not reaching for your wallet, as he grabs the bill and reaches for his (wallet), thank him – genuinely and with appreciation. 

STACIE’S TIP # 3:  Stick to your guns. 

IF your date challenges you, communicate your preference to them, using “I” statements only.  For example:  “I would feel more comfortable if you and I split the bill because I am not used to having people pay for me, although I really appreciate you wanting to.  If you and I decide that we’d like to continue to see each other, and it’s important for you to treat me from time to time then this is something I’m prepared to work on.”  It’s very difficult for someone to argue with another person’s feelings, especially when they are clearly articulated and sincerely shared.  It is also unusual that someone will force the issue with a person they do not know well.

Melissa – I hope this answers your question.  Remember, if your behaviours are not aligned with what you truly want it is you who will pay the price (pun intended) down the road.  How you behave on a first date sets the tone for the rest of the relationship.

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