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People who struggle with insecurity often feel anxious about work, school, friends, family, or their own self-image.  It can seem to come out of nowhere, or it may be triggered by past negative events.  Be open and willing to listen.  Listen to what's bothering them.  Things that seem small to you might actually be bigger, deeper issues for them.  For example, if the person is worried about the shoes they're wearing, this insecurity might reflect a larger anxiety about whether they fit in with their peers. Be non-judgmental.  Try to understand how they may feel, and what you might need if you were in their shoes. If they are hesitant to talk with you, consider just saying a few words to show you understand their feelings, such as "I'm sorry about what you're feeling" or "That sounds tough." While some insecure people may come off as rude or cold, avoid letting your own insecurities or judgments play out.  Be kind, polite, and respectful.  While it may be difficult to be this way at times, it will make it easier in the long run to deal with someone who is feeling insecure or unappreciated.  Use body language that indicates you're willing to help and listen.  Maintain eye contact and give your full attention. Smile and be open to talking with them about what's bothering them. If the two of you are friends, it's important to talk with them about how they're feeling.  If they are acquaintances to you, consider ways to be more open and talk with them, without making them feel uncomfortable.  Consider starting the conversation in a general way, but then point out something that you've noticed in them.  For example, "Hey, how's it going?  I noticed you didn't come to practice after school yesterday, and wondered if you're doing okay?" Be open to the fact that some people may not feel ready to talk about what's bothering them, but it's important to show that you're concerned.  For example, "It looks like it's been a tough day.  If you want to talk, I'm here." If you need to stop the conversation, then use polite words and say something like, "It was nice to talk with you.  Okay if we catch up more tomorrow?" or "I hope you feel better.  I'm free to talk more the evening, if you'd like." Sometimes, insecure people feel underappreciated or unloved.   By showing an interest them, you may help them to feel better.  Spend time with them one-on-one if possible.  You may be able to see what's bothering them in a more real way.  Insecure people are less likely to be open and honest in larger crowds. Consider asking them to do things with you and your friends.  Make them feel included. Show that you care with your words and actions. Demonstrate that you are emotionally connected to their feelings and insecurities in a genuine way.  Say things like, "Just know that I'm here for you and care about you" or "I know you can overcome what you're facing. You're a strong person." If this person is a close friend, family member, or partner, consider giving hugs or other forms of affection as appropriate. Only hug them after asking first and if they are open to this. Tell them it's going to be okay, and things will get better.  Provide hope and motivation to succeed rather than reminding them of the bad things.
Understand their perspective. Be kind and respectful. Ask them about what's bothering them. See opportunities to get to know them better. Provide reassurance and empathy.