28 Oct How to Deal With Insecurities in a Relationship
You were fine about all of this at forty. Now you are fifty-six, five months into something that is going well, and you have spent part of this morning wondering what his ex-wife looked like.
This is not a confidence problem, which is how it usually gets described and why the usual advice is so unhelpful. It is a comparison problem, and comparison has specific mechanics that can be interrupted.

What you are actually comparing yourself to
Four candidates, and they need different handling.
His previous wife. A person you have never met, assembled from three anecdotes and a photograph on a bookshelf. The version in your head is not a real woman and cannot be competed with, because you built her.
Yourself, twenty years ago. The most common one and the least often named. The comparison is not with another person at all but with a version of you who had a different body and more certainty.
Other couples. Including, increasingly, the ones on a screen. Pew Research Center found that among single-and-looking social media users who see other people’s relationship posts, a third say it makes them feel worse about their own dating life, and that women report this more than men, at 40% against 28%. This is not a young person’s phenomenon and the material is not representative of anything.
An imagined woman he could have instead. A woman with an easier life and grown-up children who call. She does not exist and she is undefeatable, which is the point of her.
The distinction that matters most
Before doing anything about the feeling, work out which kind it is, because one of them is useful.
Insecurity as weather. It arrives without a cause, is worse when you are tired, attaches to whatever is nearby, and recedes. Nothing he does changes it for long.
Insecurity as information. It has a referent. He is inconsistent, or vague about his week, or warm in private and distant in company. In this case the feeling is doing its job and the problem is not in your head.
The way to tell them apart is to write down what specifically happened in the last fortnight. Weather produces a blank page. Information produces three incidents, usually in under a minute.
People at this stage of life are often so braced against being paranoid that they systematically discount the second kind. Having been accused of insecurity in a previous marriage is not evidence that you are being insecure now.
The reassurance trap
Asking for reassurance works. That is the difficulty with it.
The relief is immediate and lasts a shorter time with each repetition, so the interval shortens and the dose has to increase. By the fifth time, he is reciting, you know he is reciting, and the recitation proves nothing except that he has learned the required words.
There is a worse version where reassurance gets sought indirectly, by running yourself down so that he has to disagree. It works once and it trains both of you badly.
The alternative is not stoic silence. It is saying the thing once, as information rather than as a question: “I get odd about his wife occasionally and I thought you should know rather than guess.” That requires no answer, which is precisely why it helps.
What actually helps
Stop collecting. Looking at photographs, reading things, asking questions whose answers you do not want. Each retrieval gives a small relief and enlarges the appetite, which is the same loop described in our note on how to stop overthinking a new relationship.
Be specific when it spikes. “I am not enough” is unfalsifiable and therefore unanswerable. “He did not reply for six hours on Thursday” is a fact, and facts can be checked against the other things you know.
Keep the parts of your life that are not him. Early relationships at this age have a tendency to absorb the whole week, and a life with only one thing in it makes that thing enormous. This is practical rather than philosophical.
Give it a year. Most of this fades as evidence accumulates, and the honest reason it is bad at month five is that five months is not very much evidence. Some of what feels like insecurity is just the ordinary unsteadiness of early dating after a long marriage, which we take separately in our note on dating nerves after a long marriage.
Get help if it is running your week. If this is taking hours a day, or you are checking things, that is worth talking to a therapist about, and it is an ordinary thing to do rather than an admission of anything.
Frequently asked questions
Should I tell him I feel insecure?
Once, plainly, framed as something about you rather than as a request for him to fix it. Most reasonable men find this easier to hear than the alternative, which is a series of unexplained moods they are expected to decode.
Is it insecurity or is he actually doing something?
Write down the last fortnight. If the page stays blank, it is the feeling. If three specifics appear immediately, treat them as observations and raise one of them rather than the general unease.
I feel worse about my body than I did at thirty. Does that count?
It counts and it is extremely common and it is worth separating from the relationship, because it predates him and will outlast any amount of reassurance he can supply. Worth noticing, too, that a man of the same age has usually arrived at the same thought about himself and said nothing.
How do I stop comparing myself to his late wife?
Mostly by not gathering more material, and by accepting that the comparison will recur for a while rather than ending cleanly. What tends to shrink it is accumulating your own history with him, which takes time and cannot be hurried.
He says I am insecure. Is he right?
Sometimes. Also worth noting that the word is occasionally used to end a conversation rather than to describe anything. Check whether what you raised was specific and proportionate. If it was, the label is doing work the argument could not.
Starting from solid ground
A good deal of early insecurity is not about self-esteem at all. It is about not knowing what you are dealing with: whether he is seeing other people, whether he means what he says, whether he is actually finished with his last marriage. Those are answerable questions and a matchmaker answers them before an introduction rather than leaving them for you to infer from the spacing of his messages. It does not remove the ordinary unsteadiness of liking someone. It does take away the part of it that is simply missing information. If you would rather begin there, you can apply for a consultation.
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