Should I Date Them? 5 Questions to Ask Yourself First

Dating around can be exciting, but it can also be genuinely overwhelming. At some point with someone new, the question shifts from “is this fun” to something bigger: should I date them, really, as in commit to seeing where this goes? That’s a real decision, and it deserves more than a gut feeling made at 11 p.m. after a good text exchange.

If you’re still turning over should I date them right now, here are five things worth asking yourself, honestly, before you decide.

1. How Do They Treat You?

This one tells you a lot, not just about them, but about how they actually feel about you. If they treat you the way you treat them, and the way you want to be treated, that’s a real sign of a good match. If you find yourself questioning why they act a certain way, or feeling a little worse after time with them, that’s worth paying attention to instead of explaining away. If this is a pattern you keep running into, not just with this one person, relationship problems counseling can help you get some clarity from outside your own head.

2. Do They Try to Change You?

A big part of being in a relationship is having someone who’s there for you and actually accepts who you are. They might encourage you to grow, and that’s a good thing, but there’s a difference between encouraging growth and trying to reshape you, especially the parts of yourself you actually like. If you notice yourself shrinking or editing who you are to keep someone comfortable, that’s worth naming to yourself early.

3. Do They Fit Into Your Life?

This is someone who would become part of your actual life: your work, your friends and family, your goals, all of it. Ask yourself how they show up in those parts of your life, and whether that’s the way you want or need them to. They should be supportive of your goals and values, and you of theirs. Sharp disagreements about how you each see your life or where it’s headed are a real flag, not a small one. If you can picture them fitting in, genuinely, that tends to be a good sign.

4. Do They Make You Feel Safe and Secure?

Emotional and physical safety aren’t extras, they’re the baseline that makes it possible to actually relax with someone. You should feel like you could turn to them if you needed to and trust that they’d show up the way you’d hope. The Gottman Institute, which has spent decades researching what makes relationships last, points to this same idea: trust and safety get built by how two people actually treat each other day to day, not by how a relationship feels in its best moments.

5. Do They Make You Feel Cared For?

The point of a relationship, traditionally, is to fall in love and build something together over time. Love and care tend to travel together. If someone is making you feel genuinely cared for now, that’s a solid indication they’ll make you feel loved further down the road too, if they don’t already. How someone makes you feel isn’t a minor detail here, it’s actually one of the more reliable things to pay attention to.

What If You’re Still Not Sure?

Sitting with these five questions and still landing somewhere in the middle is normal, and it doesn’t mean you’re doing this wrong. Should I date them isn’t always a question with an obvious answer right away, some of it only becomes clear with a little more time. What matters is that you’re actually asking, rather than drifting into something without checking in with yourself at all. And if you do decide to move forward, know that healthy relationships still take ongoing effort, couples counseling exists for exactly that kind of maintenance, not just for relationships already in trouble.

Remember to Love Yourself Above All Else

Figuring out whether you want to be with someone can feel confusing, and wanting to get it right for yourself is completely valid. These questions are meant to help guide that decision, but give yourself some self-compassion along the way too. Nobody knows exactly what the future holds, even with the most careful planning. Do what you can to prepare yourself, and then let some of that pressure go. Choose what actually makes you happy.

Still Asking “Should I Date Them?” Let’s Talk It Through

If you’re working through relationship questions, whether that’s this one or something bigger, Book a 20-Minute Complimentary Consultation with one of our licensed therapists. Prefer to talk it through by phone first? Call us at +1-888-661-2742.