Often, women will feign a desire to split the cost with you out of politeness by executing “The Reach,” where they motion toward their wallet — but what that really means is that it’s time for you to insist.

As dating evolves, and men meet women not at weddings or water parks, but over hook-up apps on their smartphones, many of the classic rituals associated with courtship are falling by the wayside. But one that refuses to fizzle out is the notion that men pay for dates. Even as women have become an equal part of the workforce, recent studies have shown that many still expect men to fork over the dough for that overpriced plate of gnocchi they just inhaled. Because women today are just as capable providers as men, the notion that they should expect every date to be paid for feels somewhat out of touch with our current economic landscape. The truth is, there is no final answers to this age-old social conundrum. Like most dilemmas, your approach to solving it should always depend on the circumstances that surround it.

The First Date
If it’s your first date, the general rule is that you should always pay. There’s really no way around it, and you can thank chivalry — which, contrary to popular belief, isn’t quite dead yet — for that. Although most women no longer depend on men to provide for them, especially not at the nascent stages of a relationship, they like to know that they’re getting involved with someone who is self-sufficient, as opposed to a deadbeat who still relies on his mom’s debit card to feed and dress himself. For those of you who are in a financial dry spell, don’t let your empty pockets dissuade you from dating altogether. Just keep the date casual. Sure, my friend just spent $200 on a second-date vodka tasting, and yes, the woman he went out with was very impressed. But said friend has a generous salary, so, although he bit his lip while throwing down his card, he could still afford to do so. If you can’t, there are a lot of alternatives to bank-busting spirit tastings. The last time I checked, a walk in the park is free, and if you’re feeling generous, two soft serves will run you about five bucks.

How To Avoid The Conversation
It’s normal to dread the conclusion of the first date, when the check arrives and the social chess match begins. Often, women will feign a desire to split the cost with you out of politeness by executing “The Reach,” where they motion toward their wallet, but what that really means is that it’s time for you to insist. When this happens — and trust us, it will — simply let her know that this one’s your pleasure. If you don’t pay, there’s a good chance you won’t be seeing her again. One way to avoid this awkward exchange, in which both parties are essentially acting out a scene whose conclusion is predetermined, is to approach your server at some point during the date and leave your card with them. When the check arrives, it will have already been paid for, the cliche charade of going Dutch will have been avoided, and you’ll come off looking like you’ve been here before.

The Second Date
If there is a second date, it means you’re interested enough to risk another pricey night out. But unless you feel absolutely inclined to do so, paying for round two isn’t necessarily gospel. But it can definitely be beneficial. Make no mistake, a woman won’t refuse your offer to pay again (everyone loves being treated), but if you accept her offer to go Dutch, she shouldn’t be overly surprised. Most women will admit to wanting and even expecting the man to pay for the first few dates, but if they want equality in the workplace, then they should be perfectly fine with equality in the restaurant, too.
If you notice that she does seem taken aback, try confronting the issue directly. Ask her what she thinks about the many rules that are implicit in dating, and who knows — maybe you’ll end up engaging in an enlightened conversation about gender roles in contemporary society. Things might also go completely off the rails, but hey, at least you’ll have a great story!

The Relationship
Once you’ve reached third date territory, both of your financial situations should be relatively evident to one another based on clues that you’ve picked up on during the first two dates. How you proceed should be based on these clues. If you have cash to blow, there are few things more worthy than blowing it on a girl you really, really like. If you don’t, and she does, let her pay. If this girl eventually becomes your girlfriend, you’ll be thankful that these issues were resolved early on in the relationship, rather than letting them fester. I have friends who are months into their relationships, and they’re still stuck paying for every drink, every dinner, simply because no precedents were set early on. One of the benefits of being in a relationship is that no topic — except maybe your addiction to pornography — should be off-limits. If you feel uneasy about picking up all the tabs, just say something! Couples should practice alternating, so as to avoid creating any resentment, which tends to fester and spread to other areas of the relationship. Remember, a couple that pays together, stays together.

Source: AskMen