Dating an insecure guy. Help needed.

I’m dating a wonderful man, who is funny, kind, and respectful. He’s caring and a great listener. The problem is, no matter what I say or do, he is always questioning if things between us are ok. He literally asks once or twice a week if things are good between us.

I text him in the mornings to say hello, we see each other most every night, I make sure to give him compliments of how sweet or thoughtful he is (being specific as to why I think that) and make sure there is a lot of physical touch, whether it be kisses, holding hands or sitting close, pressed up against him.

We’ve been intimate and I’ve shared how it made me feel being with him. I even send him suggestive text messages once in a while. We’ve talked specifically to say we only want to date one another and are not looking for anyone else.

Still – he asks frequently if everything is good between us.

What am I doing wrong? I’ve never dated someone so insecure. I’m trying to have patience, but it’s really taking a toll on me. I’m feeling like I’m putting forth all the effort in the relationship and only being questioned in return.

He's pretty negative about himself. I try to encourage him, but it's really wearing on me.

Any suggestions would be appreciated.

it must be hard for another person to be constantly building up another's ego. low self esteem could cause the other person to need constant stroking. i would try to tell this other person to please try to understand that things will always be good and there need not be any questioning about it. if they need proof, tell them you are still with them.good luck

It doesn't sound like you're doing anything wrong. You're attentive and forthcoming with your feelings. The best thing to do would be to let him know that he doesn't have to ask about how things or going or fear that you're losing interest. Tell him if there is anything to concern himself with, that you'll bring it to his attention.

Are you intimate enough to ask him why he feels like this? Or will it sound intrusive as hell? How long have you been seeing each other? Communication is the key here. Does he talks to you about his feelings or is he closed off?

I have self-steem and trust issues. I'm constantly expecting my bf to find someone better than me, not to mention my brilliant potential to perceive every wind change and fallen leaf as the most logical sign that he doesn't like me anymore. I know, from the bottom of my heart, that it's frustrating, but I can't help it. You're probably not doing anything wrong.

Just saying, this doesn't work for me. Lol. I'm 100% sure I'm a piece of ****, it's not a matter of people letting me know something is wrong or not... it's more like a constant "have you already realized it and this is when I'm supposed to completely detach from you and never talk to you again?" feeling.

Hi Kelly, you're not doing anything wrong.

I really feel for your bf. I know what it's like to be an insecure man, I'm one too. These things come from when we were little boys, growing up, some or other male figure in the boy's life usually acts like an emotional abuser and spirit-breaker of some kind. Hence the useless and insecure feelings. In many cases, it's the dad.

It's really sad. The worst thing is you can tell us a thousand times you love us and we are OK or wonderful, we can never get ourselves to believe it.

I can tell he loves you very much and you are probably the best thing that has happened to him in his life or in a long time. All those childhood fears return in such a case, he is so scared of doing something to screw it up and losing this one person he loves, hence his constant asking.

I think I know exactly where his fears are coming from. He was abused by someone who had an extremely narcissistic and fickle personality, who always believed they were right. The slightest "error", deviation from the iron-clad rules or even simply an alternative viewpoint is heavily criticized and a lot of guilt is laid down on that person for daring to do such a thing. I know this all too well. This abuser is a control-freak and highly insecure himself, and anything not the "norm" is immediately heavily criticized and contested, even if it's right. You learn to walk on eggshells around such a person, never knowing when you are likely to screw up again, all you know is, at some point, you definitely will, and each time it is an extreme guilt-trip and a heavily emotionally tormenting experience.

We never really recover unfortunately, the effects minimize over time, but it requires a lot of things in his life to build his confidence back up. For me, I try teaching and I'm planning to finish my PhD and open my own company one day. If I can achieve those things, I'm hoping it can fix me somewhat.

Maybe encourage him to go for a dream he always wanted to achieve, and then if he sees you support him 100%, it might restore his confidence.

I wish you all the best.

You could challenge him to go a certain period of time without asking that question.

Have him talk to someone about his issues and have him talk to you about what's been bothering him most. Then listen, you're currently doing everything right. He needs assurance, but searching a certain kind of assurance of some way to reach out to you he is not comfortable doing or feeling like he is certain what he feels.

I've been in similar shoes, but that's how I used to do it, I wouldn't do it, because I'm worried, I don't care what the other person did would leave me or hurt me. I just wanted to feel safe from something that went wrong in my life, and needed someone's assurance, because I didn't received it when I needed it.

but I could be wrong altogether and he justs wants that certain attention like he gets a satisfaction out of making you guilty to come to his needs and if you don't he'll feel disconnect and worried about stupid ****.

I don't think he's a bad guy nor do I think he's reached that point. I'm just saying if he is willing to let go of his insecurities he'll find his own way to do that, and you must let him have room to do that.

If he is really insecure and looking for reassurance, this is not a good idea in the first moment of confrontating the issue.

As someone else said, unless he's being manipulative or something, it's not like he is comfortable with being like that and probably feels inadequate at some point, so this could feel like shaming.

Then again it absolutely might just work. IF the person receiving the request has enough trust in the person relaying the message.


I wasn't as intense as the bf being described here, but I too needed reassurance, way too often, and seemingly without reason.


Bf and I had a good talk, he reminded me that he's a very honest and direct person, and that if I ever did do something that threatened our relationship, or if there was something else threatening it, well he assured me that I would be the first to know.


No beating around the bush.


That was admittedly not an easy pill to swallow, but I trust him, and I managed to swallow the damn pill with a little creativity.


I created an evidence box full of mementos, emails, cards, rose petals, etc that served to remind me that he wasn't about to run.


In time I needed the evidence less and less and now I don't at all.


Me learning to take my bf's word for it (plus my secret weapon) helped our relationship immensely. I no longer feel like there's a timer attached to us and that I have to check in with him to gauge how much longer we have.

Yup. That's why I asked how close they are. If they're close in an emotional, trustful way, then I think this is actually their only option.

It happened to me too, it wasn't easy and it's not like I'm completely over it... but it helped me a lot. I don't trust other people so it was a big advance in my life.

The situation strikes me as similar to many other anxieties. A person feels anxious and asks for reassurance. If the reassurance is given, the person never learns to judge the situation for her/himself and never learns to tolerate those feelings of anxiety.

A slightly different approach would be to accept the question but decline to answer. So when he says "Are we okay?" a response could be "What do you think?".

Presumably he will say "I don't know, that's why I am asking."

Then one could say "Is there evidence that we are not okay?"

The idea is that he then is expected to produce evidence or realize that he doesn't have any. If he produces "evidence", that can be discussed and he can learn what constitutes actual information about the relationship. If he has no evidence, you can simply say "Okay, let me know if you ever have any actual evidence."--without giving him reassurance.

Over time, he can learn to look for evidence one way or the other, rather than simply turning to you for reassurance.

Thanks everyone for your input.

Bill3 - thanks, that was very helpful. I will try that approach.

Hi Kelly,

I am glad you are seeking advice on how to fix this issue and to support your boyfriend. Like your boyfriend, I am insecure; however, I am extraordinarily passive so I never reach out for self assurance like he does. Since I rely entirely on others to gauge my self worth (I know this is wrong and I am beginning to work on "me"...), I have allowed a nearly six year relationship with my fiance to fall apart in the absence of the support I needed but did not know how to address. Your awareness will benefit the both of you-- I wish you so much luck and love in your relationship.