Dating an insecure woman: 15 tips you need to know

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Are you dating an insecure woman and have no idea how to deal with her emotions? 

Then this is the article for you. 

At the start of my relationship, I was riddled with insecurities and low self-esteem.

My boyfriend didn’t know how to handle it. He tried his best, but it was tough for both of us. Four and half years later, we’ve finally figured it out. 

Now I’m not the same woman he met. I’ve grown in the last four years, embraced the woman I am, and put many of my insecurities behind me!

But I couldn’t have done it without his support. So, if you’re dating an insecure woman, read on to find out how you can make it work! 

1) Read up on insecurity 

You’re dating a girl you really like, but she’s insecure and it’s possibly off-putting for you. 

I get it – insecurities aren’t pretty.

But the truth is, we all have them to varying degrees! Yes, you too will have your own insecurities. 

So, before you go any further with this girl, you need to do your research. 

WebMD describes insecurities as:

“A feeling of inadequacy (not being good enough) and uncertainty. It produces anxiety about your goals, relationships, and ability to handle certain situations.”

I encourage you to read up as much as possible. My boyfriend initially thought I was just dramatic, jealous, and moody. Once he realized where it stemmed from, his entire outlook changed. 

And so did mine! The research helped us both understand what I was going through and how to deal with it. 

2) She needs your support 

Now, once you’ve got up to speed on what insecurity really is, you should be in a better position to support the woman in your life. 

So what do I mean by supporting her? 

I don’t mean that you have to baby her or pander to her every need. She’s a grown woman and it’s not your responsibility to take on a parental role. 

But here’s what you can do instead: 

  • Listen when she needs to talk
  • Don’t judge her or laugh at her fears 
  • Help her see things from a rational perspective rather than the insecure view she’s used to 
  • Hold her and make her feel safe 

The truth is, everyone wants a supportive partner, but if you’re dating an insecure woman, you’ll need to go that extra mile. 

So a word of warning; if your heart really isn’t into it, do the kind thing and break things off now. 

Only continue if you genuinely want to be with this woman and are willing to put in the hard work! 

3) Patience and trust building are essential

We all know the importance of trust in a relationship. With an insecure woman, this importance is doubled. 

And there’s a catch…

You’ll have to work harder to earn her trust and wait longer for it to happen! 

Depending on why your girl is insecure, she may struggle to bring down her barriers. 

If she’s anything like I was, she’ll be waiting for the moment you screw up to confirm her belief that no one can be trusted. 

It took me the good part of a year before I finally started trusting my boyfriend. And to his credit, he never did anything to make me doubt him. 

Other girls? He paid them no attention. 

Fear of him leaving after a fight? He always came back to make up. 

Waiting for him to break a promise? Four years later and I’ve given up waiting. 

If you really want her to trust you, it’s simple…

Be trustworthy! 

And patient. It’s a long road ahead but it’ll be so worth it when you finally do earn her trust.

4) Be a consistent person in her life 

Now, continuing from the last point, one of the best ways to help your insecure woman trust you is to be consistent. 

WebMD also mentions insecurity:

“…Might stem from a traumatic event, patterns of previous experience, social conditioning (learning rules by observing others), or local environments such as school, work, or home. 

“It can also stem from general instability. People who experience unpredictable upsets in daily life are more likely to feel insecure about ordinary resources and routines.”

So why is being consistent important? Here are a few key reasons:

  • It builds trust within the relationship 
  • It creates a sense of security and safety 
  • It shows your partner they can rely on you 

All of the above are super important for an insecure woman. We need to feel like we can depend on you, and that you’ll follow through with whatever you say you’ll do. 

If you don’t, it creates a lot of doubt in our minds. We start to wonder what else you’ll bail on. This much uncertainty can send us into a downward spiral. 

So, if you’re determined to win the trust of your girl, start with consistency. 

Check out this guide I came across, it’s got some great tips and examples on how to improve consistency in relationships. 

5) Reassurance will be your best friend 

Now, there’s one thing you’re going to have to do, and you may not like it. 

My boyfriend certainly didn’t at the start, especially when it came to ex-girlfriends. I was incredibly insecure about the fact he was still friends with a couple of them. 

I needed A LOT of reassurance. 

But now I’m at a place where I’ve even become friends with them! 

Your girl may not have the same issues, but for sure she’ll need reassurance about something. 

Want my advice?

Just do it. 

I know, I know, you shouldn’t have to. In an ideal world, you wouldn’t have to. But you’ve chosen this girl, and there are certain things you’re going to have to accept if you want a future with her. 

Reassurance is one of them. 

So how can you effectively reassure her (without going crazy yourself)?

  • Listen to her concerns with an open mind and show a willingness to understand how she feels 
  • Speak clearly and calmly. Don’t beat around the bush or use terms like “You should know this already without me telling you.”
  • Back up your reassurance with evidence. If you want her to believe you really do care about her, gently remind her of all the ways you’ve displayed this care.
  • Acknowledge how she feels but be confident and firm in letting her know everything will be okay. While her mind is spiraling, she needs you to be her anchor!

6) Be a confidence boost in her life

Every time I said, “I can’t possibly do that” or “I think I look so bad in this outfit”, my boyfriend was right there to boost my confidence. 

Many articles will tell you to move straight on if you meet an insecure woman. She’ll never change, they’ll tell you. 

Well, I’m proof anyone can change. And whilst a lot of the work on my confidence was done by myself, I have to give a lot of credit to my boyfriend! 

Instead of judging me for being so doubtful and insecure, he simply believed in me. And he was vocal about it. 

And you can do the same for the woman you’re dating. If you truly believe she can be a confident, strong, self-aware woman one day, help her see it too. 

  • Encourage her to go for her dream job
  • Open her eyes to her wonderful quirky personality 
  • Love on her whenever she’s feeling insecure about her appearance
  • Praise her when she takes on a challenge 

The sad truth is, many insecure people have simply never had anyone around who allowed them to be themselves. Who believes in them without reservation. 

Just imagine how she’ll bloom if you show her this love and encouragement…

7) Be genuine with your compliments 

Now, we know most women (and men) enjoy being complimented. Your insecure woman will be no different. 

But there’s something important you need to keep in mind:

Be genuine.

Make your compliments count. 

You don’t need to flatter her every time she walks into the room. She’ll quickly start seeing through it and it’ll make her distrust you. 

Instead, compliment her on things worthy of it, such as:

  • How clever she is for solving an issue
  • How brave she is for giving that big presentation at work 
  • How resilient she is for getting back up after a hard couple of days
  • How lovely she looks when she laughs 

You get the gist…

The bottom line is this:

Compliments make us feel valued and appreciated. They boost our confidence and fill us with feel-good hormones. 

8) Share your insecurities with her 

At this point in her life, your girl probably knows she is insecure. It’s no big secret, even though she may not talk about it openly with everyone. 

But showing her she’s not alone in her insecurities can help her to feel more comfortable discussing it. 

So, what are you insecure about? 

Think of a couple of things that really make you anxious. Also, think about how you deal with them. 

The next time she starts getting antsy about something, calmly explain how sometimes you feel insecure too. 

Create a safe space where you can both talk about your feelings. Then you can gently bring in what you do to keep your insecurities at bay. 

Who knows?

She may feel encouraged by your honesty and start researching how to overcome her insecurities too! 

And even if she doesn’t, your show of understanding will go a long way in helping her feel secure. 

9) Have healthy boundaries in place 

Boundaries. You BOTH need to have these in place. VeryWellMind describes these as:

“Boundaries can be described as how emotionally close you let people get to you. They are also where you draw the line within a relationship. They say how much you are willing to give or take before requiring that things change or deciding to call it quits.”

Here’s an example: 

I used to want my boyfriend to text me all hours of the day. He wasn’t comfortable with that, so he set a boundary and said:

“I’m comfortable texting at the start of the day and when I get home, but I don’t want to text while I’m at work.” 

I had a choice; either accept it or get into a fight over it. Since he later took the time to explain calmly why he didn’t want to text all day, I accepted. 

It’s important to have these boundaries in your relationship. It creates respect and allows you to take ownership of how you’re treated. 

An insecure person may challenge your boundaries, but if they really love and respect you, they’ll accept them (so long as they’re reasonable and you give them plenty of reassurance!). 

10) You can help her understand her insecurities

Some people think that once you’re insecure, you’re going to be that way forever. 

But that’s simply not true. 

You can help her overcome her issues, but first, you’ve got to dig deep and find out the root cause of why she feels this way. 

See this as a project both of you can work on together (if she’s up for it).

The truth is, I can’t diagnose your girl, but there are some common causes of insecurity. 

This article by PsychologyToday highlights these root causes and gives some tips on overcoming them. 

So, how did I get to the root of my insecurities? 

It actually came through talking. I talked a lot to my boyfriend about my upbringing. We started to see patterns of behavior linked to things that happened in my childhood. 

Slowly, slowly, we were able to unpick how these insecurities formed. 

It was a long process but we did it for each other. It strengthened our relationship but also gave me a starting point on how to resolve my issues. 

11) Never bring up her insecurities during an argument 

In the heat of the moment, you might be tempted to throw her insecurities back in her face…

Here’s why you shouldn’t do it:

  • She’ll regret confiding in you in the first place
  • She may shut down in future conversations 
  • She’ll resent you for bringing up her insecurities whilst she’s in a vulnerable state 
  • She’ll trust you less 

Do I need to say more? 

We’ve all been there, we’ve all said things we shouldn’t. But with an insecure woman, she’ll hold onto your nasty remarks for a long time. She’ll internalize them. 

You’ll literally be undoing all the hard work you’ve put in to help her overcome her insecurities! 

Now, if you do need to bring it up, perhaps because the argument is a result of something she’s insecure about, do it after the argument, once you’ve both cooled down. 

It’ll be a much more productive conversation than if you bring it up in the heat of the moment. 

12) Don’t brush off her insecurities as trivial 

And on the point of bringing up her insecurities, it’s important not to sweep them aside either. 

Downplaying someone’s feelings can be incredibly hurtful. It can actually contribute to having more insecurities. 

Psych Central explains the consequences of emotional invalidation:

  • Emotional invalidation can lead to confusion, self-doubt, and distrust in your own emotions.
  • People who feel their emotions are invalidated often hide their emotions and develop low self-esteem.
  • Emotional invalidation can contribute to someone developing a mental health condition, such as depression and anxiety. If you already have a mental health condition, it might make your symptoms worse.

It’s pretty clear to see that if you ignore or dismiss your partner’s insecurities, it’ll only make them worse. 

Instead, re-read point number 2 in this article (on how to support her). 

And remember – even if you don’t understand why she feels the way she feels, it doesn’t hurt to be kind and avoid judgment. Trust me, she’ll appreciate it.

13) Avoid picking up her insecurities 

Now, this point is aimed directly at you. 

We’ve spoken a lot about your insecure woman, but there’s something important you should know:

You need to protect yourself from picking up her insecurities. 

Think about it:

You’re together most of the time. You’re intimate, you share your thoughts and feelings. It’s only natural that you’ll rub off on each other. 

But the key is to understand her insecurities, and realize that they aren’t your own! 

This is where boundaries (I talked about this in point 9) will come in handy. If she’s freaking out over something, you don’t have to join in. 

You can be there for her, but you shouldn’t let her worries seep into your life. And if it does start to happen?

It’s okay to take a break sometimes. Spend time with friends or family. Go for a run or do something alone. 

We all need time to recharge our batteries and recenter ourselves! 

14) Don’t focus on just the insecurities 

The point of this article wasn’t to paint insecure women as needy, obsessive, or clingy. 

It wasn’t to put you off from having a relationship or dating her. 

It was purely to help you be a source of support in her life! 

Because the truth is, something attracted you to her. 

Whether it was her looks, personality, or how she makes you feel, you’ve got a connection. 

And her insecurities don’t have to get in the way of that. 

So, whilst it may feel heavy to process all this information, I’d like to remind you to focus on the good stuff too! 

If you can do that, and help her do the same, I believe you can overcome her insecurities (and yours) together. 

15) She may need professional help 

Now, it’s important to note that I’ve spoken about women with a “normal” amount of insecurity (that most people live with daily).

But if the woman you’re dating is so insecure to the point she can’t function on a daily basis, she may need more than just your help.

In this case, she needs to see a therapist or psychologist. 

You can suggest this to her, in a non-confrontational way, but you can’t force her. 

If she decides to go, great! You can be there to support her. 

If she doesn’t, and it’s really putting a strain on your relationship, you may need to think of yourself and move on.

But if you think she can overcome her insecurities, show her the love she doesn’t think she deserves. 

Together and as individuals, there’s no reason why you both can’t become stronger. 

Not only will you learn more about yourselves, but putting in that hard work now means you’ll get to know each other on such a deep level. 

It’s this type of foundation that can then lead to a great, long-lasting relationship

Can a relationship coach help you too?

If you want specific advice on your situation, it can be very helpful to speak to a relationship coach.

I know this from personal experience…

A few months ago, I reached out to Relationship Hero when I was going through a tough patch in my relationship. After being lost in my thoughts for so long, they gave me a unique insight into the dynamics of my relationship and how to get it back on track.

If you haven’t heard of Relationship Hero before, it’s a site where highly trained relationship coaches help people through complicated and difficult love situations.

In just a few minutes you can connect with a certified relationship coach and get tailor-made advice for your situation.

I was blown away by how kind, empathetic, and genuinely helpful my coach was.

Click here to get $50 off your first session (exclusive offer for Hack Spirit readers).

Kiran Athar

Kiran is a foodie, writer and traveler. She considers herself a citizen of the world, who gets her inspiration from the people she meets along her journeys. She's currently living in Spain, where she spends her time writing, watching the shepherds and eating tapas in the mountains of Andalucía.

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