How to Date Someone Who Needs Constant Reassurance

It’s a strange situation to be in: you meet someone great and sparks are flying but your new love can’t seem to get comfortable. They always seem to have questions about how you feel about them, or why you aren’t available to see them more often. They may even take it to the next level and ask you if you’re cheating on them.

There’s no denying that it’s a stressful situation to be in. You really like this person, but you can’t seem to get that message across, no matter how hard you try. Why won’t they trust you?

If you really like this person, you may want to know what you can do to let them know you like — or maybe even love — them. Finding out what’s motivating their insecurity is the key to learning how to date someone who needs constant proof that you care.

First option: Work on your communication

The first step in figuring out how to date someone who needs constant reassurance is to make sure you’re communicating as well as you think you are. People have different ways of expressing themselves. Some people share affection through words, while others show love in their actions — ideally, people will balance both, but some people tend toward one or the other.

Is it possible that your communication style doesn’t match your partner’s? They may be feeling insecure because you’re used to showing affection by doing things like paying for dinner or helping with repairs around the house. In fact, you may be feeling a little underappreciated because they’re telling you they care without really showing it.

While it’s definitely a good idea to try to make the person you’re dating feel at ease, that doesn’t mean that you should have to change who you are. As in all parts of live, compromise is key. If you can give a little, maybe they can give a little too, and some of that uncertainty may dissipate naturally.

Option Two: They’re suspicious

What kind of reassurance is your partner looking for? Do they want to know where you’ve been, who you’re spending time with? Maybe they’ve even asked you outright if you’re seeing other people behind their back.

There are many reasons why a person has trouble trusting other people, and there are very few of them that you personally can fix. Often, people who have difficulty trusting others in relationships have been hurt in past, or grew up in a household where they witnessed their parents being dishonest with one another. Obviously, you can’t go back and fix the pain they’ve experienced in past…

…and obviously, telling someone you’re dating that they’re in need of therapy is a pretty risky proposition, too. However well you mean it, and however true you know it to be, some people see the need for mental health care as a weakness. Until the stigma against mental health care starts to fade, the key here is — once again — to communicate.

Explain to them that they have nothing to worry about. Let them know that you care, and that they can trust you to be honest with them. It may take time, but they may eventually start to take you at your word.

However, keep in mind that the give-and-take of a relationship — even just dating — means that you need to be treated with respect and have a right to maintain boundaries. If the person you’re dating is asking to see your texts, or calls you constantly to find out what you’re doing, that’s over the line. No matter how much you like a person, that behavior isn’t acceptable, and if they won’t respect those boundaries, you need to think twice before continuing to date them.

Option Three: They have low self-esteem

Everyone is a little insecure about something. Some people feel they aren’t smart enough, while others feel they’re not attractive enough, or may even think that they’re not worthy of love at all. If it reaches a point where the person you’re dating begins to wonder why you’re interested in them at all, you may be wondering what to do.

Again, you can only do so much. You can try to reassure them, but it’s very possible it’s their processes and not your actions that are the issue.

Try asking them the very basic question: What can I do to reassure you once and for all that I care?

They may not have an answer for you, especially if it’s their own insecurity that’s to blame. You can tell them they’re smart or attractive or funny all day, but you can’t make them believe you. It’s time to revisit the communication issue: is there a way to help them feel more cared for without compromising your own values? Low self-esteem is rarely completely fixed by a communications tweak, but if they tell you they’d like you to be more vocal about complimenting them, that’s likely an action you can take.

Summing it up – Stay strong or breakup?

If someone needs reassurance so often that you’re nearly exhausted in trying to keep them happy, it’s worth considering if you want to continue dating them.

Insecurity isn’t a sin, but you have a right to a fulfilling relationship, too, and constant reassurance may be more than you signed on for. If you decide that the insecurity or suspicion is too much for you, be direct but gentle when you call things off (Our breakup guide may be of help to you).

This may feel like it’s hard to do — the old “it’s not you, it’s me” will be hard for the other person to see. They may blame themselves, or they may be convinced that they were right to be suspicious of you. This won’t feel good to you or to them, but all breakups are hard, regardless of reason.

But on the other hand, a little communication goes a long way, and you may find that some very simple, straight-ahead questions can make the person you’re dating feel a little more comfortable in the long run. Let the person know you care, and the rest will sort itself out.

Photo of author

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.