Dear Anna,
I’m a 40-year-old newly divorced career gal, and dipping my toes back into the dating pool after a long marriage. I’m not looking for anything super serious just yet, but I also don’t want to waste time on people who aren’t genuinely interested or who have wildly different values or goals than I do. The idea of endless dates and surface-level chitchat sounds exhausting, and I’d love some advice on how to screen or vet people — to get a better feel for them upfront, so I don’t burn myself out. Are there any tips or tricks to avoid the time-suck of serial dating? Thanks! — No Time To Waste
Dear NTTW,
I love your approach here. Dating has changed a ton in recent years and it can be easy to feel overwhelmed or like it’s another “chore.” Getting back into dating is already a huge step, and the fact that you want to protect your time and energy shows a great deal of self-respect. Dating should be exciting, not exhausting. And while it’s tempting to jump in and see what happens, setting yourself up with a few mindful strategies can make a big difference. So let’s explore.
First things first, the “screening” mindset is key. Instead of thinking of a date as a mini-relationship audition, think of it as a chance to see if the other person aligns with your values and lifestyle. This is something that can start well before any in-person date. To kick things off, lean into a thoughtful conversation over text or email. Yes, it can feel a bit old-school, but a few well-chosen messages can reveal quite a bit. When messaging, try using open-ended questions, like, “What’s something that makes you lose track of time?” or “What are some deal-breakers for you in life?” or “What’s something people tend to misunderstand about you?” By asking direct but open questions, you’ll likely see how well they can communicate and what’s genuinely important to them. (If you need more ideas, there are tons of questions online. Or here are 50 more from me.)
It’s also a nice preview of their emotional maturity and interest in connecting beyond the surface level. Also, if they don’t ask you any questions during these exchanges, that’s another clue about them. See last week’s column on green flags to watch out for.
If you feel comfortable after initial conversations, suggest a phone or video call. Yes, it’s less common with texting being so prevalent, but hearing someone’s voice, seeing their body language, and having to hold a conversation without a keyboard can be a big tell. Are they distracted? Engaged? Can they handle some depth, or do they seem evasive? A lot of the subtleties in tone and mannerisms come through that way. As strange as it may sound, there’s a certain charm and vulnerability in video calls that can either build anticipation or help you realize it might not be worth meeting up in person.
To save yourself from endless first dates, you could also go the “half-date” route. Rather than committing to a full evening, consider meeting for a casual coffee, a dog walk, or even a quick lunch or dessert. These low-stakes, low-commitment meetups are ideal for testing the waters without dedicating an entire evening or dropping a ton of cash at a bar. Plus, it keeps things light and frees you both from any pressure of a more formal date setting.
Another tactic is to set up “nonnegotiable” qualities in your mind ahead of time. These are more than just the usual “must like cats” or “must want kids” lists. Think of them as foundational values that you truly can’t live without, like kindness, curiosity or respect. You can keep them in mind as you screen people — not to box them in, but to make sure you’re respecting your time and theirs by focusing on what matters most to you.
Some people find social media profiles to get a sense of a person’s lifestyle or verify they’re not already partnered, and while I understand the impulse, it can be a bit invasive — so much can be misunderstood out of context, and it can set up unfair expectations. Instead, I recommend trying other more direct and natural ways of getting a feel for who they are.
If your potential dates push back on these upfront steps or seem unwilling to engage in a way that’s meaningful to you, that’s a green light to move on without guilt. Someone truly worth your time will understand and appreciate that you’re being selective, just as you’d hope they would be, too.
Remember, dating is about adding joy, not draining it. So get really clear on what you want, don’t overdo it or overwhelm yourself, and trust that you’re worth the effort of finding someone who appreciates you for you.
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