By Nancy Rugart Plummer, Columnist, The Times
Dear Nancy,
I’m new to online dating and have been meeting great women, but many expect me to pay for everything—even though they’re successful professionals. I like one woman in particular, but I’m hesitant to be exclusive since she never offers to split costs. Any advice?
Pascal – 59 – Bryn Mawr
It’s completely understandable to feel conflicted. You’re dating successfully, you have a solid career, and you’re meeting accomplished women—yet you’re noticing that many of them expect you to foot the bill every time. That can feel one-sided, and it’s okay to want more balance.
Honest communication is key. Early expectations often set the tone for the relationship, so it’s important to discuss financial boundaries before frustration or resentment builds.
First, reflect on your own values around money and partnership. If equality, teamwork, and shared responsibility matter to you, it’s entirely valid to want those reflected in your dating life and beyond. Being clear about this doesn’t mean you’re cheap—it means you’re being intentional.
Rather than staying silent or feeling pressured, open a respectful, calm conversation. For example:
“I really enjoy spending time with you, and I want us to keep having fun together, but I also value a more balanced approach when it comes to expenses. I’d love to find something that feels fair for both of us.”
This kind of honesty shows maturity and self-respect—and it also gives her the opportunity to share her perspective. Sometimes people don’t even realize the dynamic feels one-sided until it’s brought up.
Several of my clients have found success by setting a monthly budget together for shared experiences. For instance, a couple might agree to spend $1,000 a month on dining and entertainment, splitting costs 50/50 or alternating who pays. When it comes to bigger expenses like vacations, you might discuss in advance what each person is comfortable contributing, or make a plan for the full calendar year.
Examples of healthy compromises include:
- Taking turns planning and paying for dates.
- One person covering dinner, the other covering tickets or dessert.
- Choosing fun, low-cost activities like cooking at home, free events, or hiking.
The bottom line? Money conversations don’t have to be awkward—just honest. When handled early and respectfully, they can strengthen trust and build the foundation for a more equal, lasting relationship. That said, if she isn’t open to sharing dating expenses or doesn’t feel she can contribute in a way that feels fair to you, it’s okay to acknowledge that your values may not align—and give yourself permission to step away and move on with clarity and self-respect.
Dear Nancy,
I just started online dating using the Match app and I’m overwhelmed with the number of likes by men! How do I go about this in a less chaotic way? I’m recently divorced and terrified of this online stuff.
Marcy – 67 – Newtown Square
Congratulations on stepping into the online dating world—especially after a divorce. It’s completely normal to feel overwhelmed at first, especially with all the likes and attention. But here’s the good news: you don’t have to respond to everyone. In fact, you only need to pay attention to the men who take the time to actually write to you.
A “like” is passive. A message shows real interest. So instead of feeling pulled in a hundred directions, simply focus on those who’ve made the effort to connect with words. This immediately cuts through the chaos and helps you prioritize quality over quantity.
Also, it’s important to know that statistically, the sooner you meet someone in person, the better the chances of building a real connection. Long message threads don’t replace chemistry, and often, over-texting leads to unrealistic expectations. So keep messages brief—enough to feel safe and curious—and then move toward meeting for a coffee, or casual drink at a place you’re comfortable. Remember, for safety purposes, always meet make your first and second dates at a public place you know.
Your goal is not to manage a digital fan club. Your goal is to meet people and discover who you feel you have a connection.
Go have some fun!
All About Connecting, It’s all about becoming the best U
Nancy is the founder of All About Connecting, and has been a Life Coach/Dating Expert for over a decade, helping hundreds of men and women transform their lives.
