How to Date an Insecure Man

Tips for Dating an Insecure Male

So you’re dating a man who makes you laugh, who actually listens to you when you talk and with whom attraction is no problem. The one problem is that this man is a little insecure, perhaps because he’s coming out of a divorce or his ex cheated on him or he’s going through a job change.

Learning how to date an insecure man who is otherwise a dream involves understanding his insecurity and tailoring your time together with empathy for security issues. It might be worth your time to help this guy through this rough patch.

I’m not suggestion you stay with a guy who has raging insecurity or who is insanely jealous. But no one is perfect and just about any relationship is going to have issues to deal with. Dating an insecure man isn’t the worst problem to have and, if you can manage that problem, trust issues will eventually go away or be mitigated in time. Here’s how you handle a man’s insecurities, increase the romance of your circumstances and make your relationship work.

1. Avoid Too Much Conversation

Guys tend to bond with other guys by doing things together: sports, games, hobbies, workouts, concerts, drinking, repairs, you name it. Highlight one or two of those activities and incorporate them into your dates, which will help the two of you bond. It’s the 21st century and physical activities can be dates, too.

Go hiking together. Roller blade or bike together. Maybe a rock climb is in order, or even a sky dive. If those are a little too extreme, consider bowling, putt putt golf or a trip to the batting cage. If you don’t like physical activities like that, then play cards and games together, or go to a concert, comedy show or sporting event together. Heck, have him come over to work out together or help you with repairs.

The idea is the two of you don’t sit down over dinner for a “date discussion”. Instead of getting to know one another in the traditional fashion – sitting and talking in the manner women tend to bond and socialize – get to know one another the way men do. Make this concession and you’ll be able to see this man in a different light, and he’ll be able to see you in a different light. Activities are a great ice breaker early in a relationship, anyway.

2. Let Him Show Off

If he has insecurities about one aspect of his life, meet him in an arena where he is comfortable, confident and skilled. Let him show off the skills and abilities he has. Not only will that build his confidence, but you might be turned on by his display of masculine skill.

This may not seem very romantic at first, but if you think this guy has the capacity to be romantic once he has his “feet on the ground”, give it time. Find out all the things he considers himself good at and pick one of them to be the focus of your date.

Once he knows that you know he’s good at a few things, he’ll be more willing to display other sides of his personality and confront his anxieties “in your world”.

3. Support Self-Improvement

Be empathic, attentive and supportive of his attempts to improve himself. If he’s going through a tough phase and he’s searching for ways to establish himself and gain confidence or learning, put all your support behind that.

Maybe he’s decided to take night courses or online courses to better his education. Maybe he’s looking to get better trained for his job. Maybe he has a dream that he’s never felt confident about pursuing, or he has a hobby he’s always wanted to take up.

If so, give your wholehearted support to these fancies. This is a great way to show him you believe in him by, well, by believing in him.

At the same time, don’t take this support too far. If you start giving him your ideas for how he can improve himself, an insecure man is going to take that as a back-handed criticism every time. You don’t want to fuel those insecurities, but to support him when he tries to become more secure about himself.

4. Build His Ego a Little Bit

A well-placed compliment never hurts with an insecure man. Complimenting a man on his skills or his accomplishments is a better way to compliment him than on his looks. Whatever he’s good at, let him know that you see his accomplishment and acknowledge it.

Better yet, let him know how he makes you feel. If he makes you feel better about yourself, if he makes you feel secure or you just have a great time when he’s around, don’t leave that unspoken. Let him understand that you respect him. Let him understand that you admire him. When a guy feels like he’s wanted and needed, that’s a major boost to his insecurities.

Also, don’t compliment other guys when he’s around, at least at first. A guy will notice if you’re the type who compliments all men and it won’t mean as much when you say it to him. Single out your insecure man for praise.

5. Be Positive and Be Diplomatic

Stay overwhelmingly positive when you talk about your needs and desires. Also, be constructive when you criticize. This is one of the ways relationships often veer out of control, is by one partner unduly criticizing and the other partner reflexively being defensive. Either one of those can make communication difficult, but if you are too critical and he’s too insecure, your romance is doomed.

So let him know the things you enjoy about your dates, your romance and your overall relationship. Be like a teacher and give him positive little tips and hints about what you like, so he will do more of those things. That’s good communication.

When there are things that annoy you about your date, the way he romances you or your relationship in general, be tactful about how you broach the subject. Consider whether it’s worth bringing up in the first place. If you do mention it, show respect in how you mention the subject. Tell him you love him (or, if you’re not that far, “you love being with him”) and then respectfully mention what it is that annoys you. Never mention the word “annoy”, of course.

6. Don’t Encourage Bad Behavior

With all of the above under consideration, remember that you aren’t to blame for his insecurity. Try to help him get over his insecurities by not pushing the buttons that some other woman pushed. That doesn’t mean you should be in charge of rebuilding his self-confidence. All you can do is help. He’s eventually going to have to help himself and heal on his own.

Also, if his insecurity appears to be growing, that’s a bad sign and you should consider exiting the relationship. Out of control insecurities can cause jealous, controlling behavior. Never encourage that kind of attitude towards you. That won’t do you any good or him any good. Reward positive actions and never reward negative (jealous, possessive) actions. Tell him in a respectful, firm fashion if you think his insecurities are starting to control the way he acts. Let him know in no uncertain terms that his jealousy and possessive attitudes will not keep you in the relationship, but cause you to leave it.

Learning how to date an insecure man can be a bit trying at times, but if he’s got a lot of other things going for him and real reasons why this insecurity is part of his personality, then it might be worth your time to suffer through it for a time. A man who has been through a broken marriage recently, who has been cheated on or who has seen his self-image damaged by career troubles might not be naturally insecure, but going through a phase. If so, you might help him end his insecurity and learn to trust again, and this insecure guy might turn into the man you’ve been searching for.

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  1. Thank you for the tips. Almost all the other articles advise girls to dump the guy. It is not so easy to dump a guy just because he is insecure. It almost seems cruel.

  2. littlefajita says:

    This is a great article!! Not many articles are out there to constructively advise women on why a man is insecure and how to go about handling it.

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