In the beginning stages of a dating relationship, there tends to be a great deal of dining out and other planned activities. While this is a fun time, it's all too easy for money (payment for activities) to create awkwardness. Here I reflect on some ways in which that awkwardness can be avoided; it is essentially a list of behaviors I have observed in men that have the potential to cause their companion discomfort. I say men because I only have a woman's perspective to offer on this subject. This reflection is not about who should pay for what, whether men should be expected to pay, and so forth. I comment here merely on behaviors I have witnessed that may be viewed as tasteless.
Let's start with a note on planning the date. I find it tremendously off-putting when a man uses the phrase “take you out” when suggesting an excursion. It is a reference to money and the most well-meaning of men do this; they use that phrase as code for “I'll pay,” but it's patronizing and downright jarring. Replace “Can I take you out to…” with “Would you like to go to…” or “Shall we go to…”. Hopefully you are dating an adult who is accompanying you to some place; she is not being taken there. I take the Kid to school or to the doctor. I do not get taken to a restaurant.
The most common situation involving payment is dining at restaurants. Ah, so many “don'ts” here… And, yes, I've seen it all. This is a non-exhaustive list of things a man should never do at a restaurant. (a) Comment on prices of menu items; for instance, “this sixty-dollar steak better be good.” (b) Tell your companion to order whatever she wants; she's an adult, she already knows she can do that. (c) Explicitly mention that you will be paying; comments such as “it's my treat,” “splurge, it's on me,” are always tacky. Once, walking around looking for dinner spots, I rejected a place for being too fancy; my companion responded “don't worry, I'm paying.” No, no….don't ever say that. Maybe I just didn't feel like a fancy place. (d) Don't look shocked or roll your eyes when you get the check, or comment on the amount. (e) Don't take forever calculating the tip amount; quickly guess twenty percent of the total even if it's not accurate. (f) Don't start going through the itemized bill; unless something looks massively wrong, don't dissect it. (g) Don't take the receipt with you; makes it seem that you are keeping an account. You can look at your credit card account later. (h) Don't pay with cash; it's inelegant and makes money distastefully visible. Relatedly, always carry a back-up credit card; it's not unusual for a card to randomly be declined. If that happens, there is no need to be embarrassed; just offer a different card.
Wine can be tricky. If picking a bottle from an extensive wine list, prices can run the gamut. I pride myself on how I deal with this situation. Having some wine expertise, I ask whether I may pick the wine. I ask my companion for general preferences (e.g. “is Malbec ok?”), and then pick a moderately priced bottle; that way, he's off the hook for picking a $300 bottle of wine and doesn't risk looking cheap by picking an inexpensive one. However, your date generally won't be so slick. You should ask her for preferences, pick a bottle that you can comfortably afford, and run your choice by her. It would be highly inappropriate for her to suggest something outrageous instead.
If you valet-parked the car, be sure to have an appropriate tip amount in cash in an accessible place (no fumbling). If she drove, let her tip the valet. My rule is: whoever drives tips the valet or pays for parking. You want to be gallant without being overbearing. Along those lines, if your date insists on paying for dinner (particularly if it's not the first date), please let her; certainly don't start grabbing the check out of her hand and arguing. And definitely don't put a stack of cash for your perceived share in front of her! No…don't do that. Actually, there should never be cash exchanges in dating scenarios.
Another area in which money comes into play is gift-giving. What do you do when you haven't known someone very long and her birthday comes up? You would like to get her a present, but have no idea what she might want. So why not take her to a store (say a boutique) and let her pick something she likes? Sounds like a good idea? No! This is a terrible idea. She is constrained by your budget, which she doesn't know. Does she look at price tags and watch your face for a reaction? Does she simply ask you? It's so very awkward! And then there is the pressure of finding something that she thinks you would like as well. What if she doesn't like anything or is an unusual size (like me) and feels that she has to find something? And then subsequently there is the expectation that you would want to see her wear it. Instead, get her some flowers and wine (if she likes wine). And arrange a nice dinner. Who doesn't enjoy flowers? Gifts don't have to be functional.
You decide you are going to cook together and go to the grocery store to shop first. If the dinner will be at her house and she starts paying at the store, there is no need to fight her. If you would prefer to pay, do it quickly before she can get her card out. But don't try to split up the items and don't try to pay her back for something random you picked up (say you needed a toothbrush). Absolutely don't try to give her cash for your items. I once had someone forcefully put cash in my purse at a store; weird and awkward and uncomfortable. Just say thank you, and remember: no cash exchanges.
On these early dates, another challenge is to find good topics for conversation. Money is not a good topic, in any context. It's not appropriate to talk about your salary, your mortgage, the price of your car, how much you pay in child support…nothing that involves revealing actual amounts. These topics are for later in a relationship, with much higher levels of closeness. As relationships evolve, discussions of money become inevitable and smoothly work their way into conversations and practices. But until that happens organically, it is best to leave money out of it and enjoy the romance.