Can An Insecure Man Date Anyone? 10 Awesome Tips To Make Date Works!

How an insecure man can start/ restart dating and make it work

By Fred S.
Can An Insecure Man Date Anyone? 10 Awesome Tips To Make Date Works!

We have all had our fair share of the good relationships and the bad ones, both of these two types teaching us some bitter realities about people and the world that we live in. We truly are a product of the events that we have been through and the circumstances that we have endured.  We have all had our fair share of the good relationships and the bad ones, both of these two types teaching us some bitter realities about people and the world that we live in. We truly are a product of the events that we have been through and the circumstances that we have endured.  

This is particularly true for dating. One bad experience, one wrong choice of a partner and one date went wrong, a single misfortune can make you lose half of your mind and make you question your sanity to the point that you either start wallowing in a deep pit of self-loathe or just grow increasingly cynical of the people around to the extent that forming and maintaining healthy relationships gets difficult, if not impossible. 

Men are marginalized when it comes to talking about their love lives, especially if they have had a bit of hard luck. The tendency for men to masquerade their emotions makes it difficult for their partners and even therapists to truly reach a conclusion about their coping mechanisms and approach towards relationships after an ugly break up. 

But, one thing is for sure, men are prone to developing an unwavering link of insecurity depending on how nasty their experience has been with someone they have been with, even if it is just for a night! This strongly opposes the prevalent idea where opposite gender assumes that men do not take the hit after a bad relationship. 

Types of Insecure Men

1. Multiple Breakup Insecure Man

These men have a hard time accepting that there is someone out there for them, owing to their multiple experiences that have all failed miserably. No matter what the reason is for their break up, they cannot seem to make their partners stay and it is not only on one of the parties. A lack of compatibility, undue expectations and the augmenting insecurity with each loss are few of the factors leading to a chaotic dating life. 

2. After Divorce Insecure Man

Many of these men took a bold step, one they might have never imagined taking, for someone they thought completes them. Turns out, the period when you are dating someone is a lot more different than settling down with all the responsibilities and finally starting a family. Sometimes, their partners end up losing interest in them in the long-run and choose to go their own way, sometimes with different people. These men have very tenacious trust issues that need to be gotten rid of as soon as possible. 

3. After Cheating Insecure Man

One of the first thoughts that continue to linger on till they are proven otherwise for men who have been cheated on is that they are not good enough and probably will never be someone’s happily ever after. They delve very deep into themselves to pick out all the specks of dirt that is within them and start to look at themselves through a very contaminated lens of not being adequate and stick with the belief that they are always in a competition to be better for someone and also versus someone. This mentality is the reason why they often end up in a state of deep depression and anger. 

10 Tips to Make Date Works for an Insecure Man

For The Multiple Break-Up Insecure Man

1. Start with the belief that sometimes you are not supposed to end up with someone because they are just pitting stops on your way to your actual destiny, which is much better and also worth all the efforts. You need to pick up a lesson as you are en-route to meet the actual love of your life. Cherish the experience of meeting new people, going on cute dates and falling in love again instead of counting all your losses.  

2. You need to step back and before you start meeting someone new, make sure that you are not blurring the lines between friendship and love. Not everyone you see, who acts kindly towards you and shows you some kind of affection, is the one. This might just be a part of their personality, learn to discern. 

3. Do not bring up all the failings of your past relationships in front of someone you have just met. Some things are just better left unsaid and not brought to light as it might irk the other, newer and better person off, giving the impression that you dwell too much on the past. 

After Divorce Insecure Man

4. Give up on the cynicism and learn to enjoy the pleasure of meeting someone new after a patch as rough as a divorce. Not everyone you meet wants to hurt you or let you down.  

5. It is OKAY to talk about your divorce, but never OKAY to make every conversation about your ex-partner and the circumstances that led to it. Your date needs to be your focus, not your ruined marriage. 

6. Be open about your dating life to your children, if you have any, giving them the idea that you are ready to move on with your life so that whenever you see someone, you do not have to worry about how your family might receive them. 

7. Remember, marriage is something you can always go through again. Do not chalk off marriage from the list or dismiss someone because you stopped believing in the institute, especially when your new partner is looking for something more serious. Otherwise, strong friction might be birthed between you two owing to your insecurity. 

After Cheating Insecure Man

8. Trust yourself and in your charisma, you owe yourself a date to meet new people and to be in a happy relationship. There is nothing wrong with you, it was just a bad relationship and it has ended now, time to explore new horizons.  

9. Nobody wants to hurt you and not everyone thinks you are a subject of comparison. You need not be overly inquisitive about their friends and exes. As stated above, no two people are the same. The person you are dating might be the one for you. Do not end up hurting them by expecting them to put you through the same nightmare as your former partner.  

10. Celebrate yourself and do not let anger get the better of you. Cheated men do tend to be overly possessive and easily agitated when they notice that their partner is doing merely a chore that divides their attention. Give your date space and let them be their own person. There is no point in projecting your history onto someone you have just started seeing.  

Memes and Quotes on Insecurity


“One of the greatest journeys in life is overcoming insecurity and learning to truly not give a shit.” ― J. A. Konrath

“Insecure people only eclipse your sun because they’re jealous of your daylight and tired of their dark, starless nights.” ― Shannon L. Alder

“A man’s spirit is free, but his pride binds him with chains of suffocation in a prison of his own insecurities” ― Jeremy Aldana


Here are some memes to send out for an insecure man.

Related Article: Dating An Insecure Woman: The Signs and Causes
Dating An Insecure Woman: The Signs and Causes

Find out the list of things that causes women to be insecure


Not all fingers are equal and no two people are the same. Also, having been in a toxic relationship should never be thought of as a pretext to find fault within oneself. As a man, you need to understand that you do not have complete control over your partner and at the end of the day they are their own people who make choices that they think to suit them the best. You cannot ever control how they feel for you and you certainly cannot make them reciprocate all the good that you have done for them in the name of love.  

Going for therapy, joining support groups and adopting a healthier lifestyle are few of the secondary things that you can consider to cleanse yourself of all the hatred that might have accumulated within you in wake of a stale relationship or marriage. Meeting new people should always be on the list, this is how you grow and also find someone who deserves the goodness in you.  Once you are able to forgive yourself, stop the pity party and realize that you are worth everything good in the world, you will be able to step back into the dating game with a rejuvenated confidence that is sure to have a more positive impact on how things go and make you cherish the happiness of being in love once again.



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