Who Should Pay for Dates When Senior Dating

If you’re wondering who should be paying for dates when you’re dating as a senior, we have some good news—you’re not alone. This is actually a very common question at all age brackets but especially for people who are in their more senior years of life.

But even though it’s a common question, it is one that takes a little finesse to answer. In this article, we’ll answer the question of who should pay for dates when senior dating, discuss the different nuances that can change that answer, and give you some tips to navigate the financial aspects of senior dating.

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Bottom Line Upfront – Who Pays for Dates When Senior Dating

The honest answer is that it depends. Many older people still hold on to chivalrous habits where it would be expected that the man would pay for the dates. However, many seniors find themselves in different income brackets during retirement, so that makes the question not that cut and dry. Additionally, you have to specify if you’re asking who is paying for the first date or who is paying for all dates because that changes it as well.

In the next few sections, we’ll talk about the nuances of this question. But before we get there, here’s our opinion if you forced us to give a more definitive answer. When it comes to senior dating and who should pay, we believe that seniors should plan to split the costs (go Dutch) on the first date. You should continue to split the costs on subsequent dates until you get a better feel for the other person’s financial situation and the seriousness of your relationship.

4 Factors that Can Influence Who Pays When Dating as a Senior

As we mentioned, the real answer in your unique dating situation isn’t going to be so cut and dry. Here are four things to consider that may influence who actually ends up paying. Additionally, we’ve included a few tips to make the financial aspect of dating as a senior a little less awkward.

1. Be prepared for a lot of people to fall on chivalrous tenets.

Many current seniors grew up in a time when the men were expected to pay for most things. If you’re dating someone who is very old school, you can probably expect them to feel this way. Here are a few tips for those that may be in this situation:

  • Ladies – It’s okay to offer to split the check. If you do, though, actually mean it and be prepared to share the costs. Times have changed and a lot of older people are on tighter budgets.
  • Men – If you’d prefer to split the check and you sense that they might be the type to expect you to pay, address this before the date. After you plan it, just say, “I always like to split the check on a first date. Are you comfortable with that?” This is WAY better handled before you’re actually on the date.

2. Want to avoid any awkwardness? Schedule a free first date.

The absolute best way to eliminate all of this awkwardness is to schedule a free first date. You can do something like going for a walk in the park, going to see a free show, or just doing something in nature. Additionally, a lot of cities have some really cool free events available for seniors.

3. Don’t schedule an expensive first date.

If you don’t want to do a free first date, that’s okay. What we would recommend, though, is don’t schedule something expensive ESPECIALLY if you’re expecting the other person to split the check. Keep it inexpensive like coffee or a drink somewhere during happy hour. There’s no need to do an expensive dinner, especially on a first date.

4. There’s a big difference between the first few dates and when you’re in a relationship.

One of the most important things to note here is that a lot of this discussion is about the first date or the first few dates when you’re getting to know each other. Once you’re in a more steady or potentially committed relationship, you can start to talk about finances a bit more openly.

At that point, you can start to get a better idea of where each of you stands. If one person is a lot more financially better off, they can consider carrying the cost of more dates (though, they don’t have to). And if you find out that you both are on tight budgets and fixed incomes, then you can plan dates that align with both of your budgets.

The Bottom Line on Who Pays When Senior Dating

Ultimately, you should plan to do what you’re comfortable with as long as it is in line with what the other person you are going on a date with is comfortable with. And if there is ever any doubt, confusion, or worry—just talk about! Open communication is great, and there is nothing wrong with being open about where you are at financially.

If you’re still not sure, though, just share beforehand that you think it’s best if you split the cost of the first date or just choose a date that’s free!

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Author: Matt Seymour, MSF

Matthew J. Seymour is a dating industry expert with over a decade of experience coaching singles, reviewing dating apps, and analyzing trends within the industry. Matt is a published author with his most recent work “Get More Dates: How to Master Online Dating Apps” that hit shelves in 2023. With a Masters of Science in Finance (MSF) degree from the University of Florida and extensive knowledge of the innerworkings of the online dating industry, Matt frequently serves in an advisory role to some of the largest dating apps on the market. In Matt’s current role with Healthy Framework, he leads the interview team that regularly interviews key dating industry leaders, and leverages his financial knowledge and dating app experience to review and share what singles need to know to get the most out of dating online.