My Boyfriend Expressed Doubts When Asking Me to Be His Girlfriend. Should I Worry?


I came across your blog when I first started online dating a few years ago in New York and your advice has helped me navigate the modern dating scene. I’ve always valued your advice because it is no nonsense, practical and mirroring worked for me like a charm.

I’m currently in a new relationship. Like you advised, I politely declined to sleep with my partner until we were exclusive. He was the first to bring up the ‘what do you want with dating’ talk, and I answered honestly that I was looking for a committed exclusive relationship. He followed up by pursuing me hard, committing to me and taking down his profile in quick succession and introducing me to his friends as his girlfriend.

He recently admitted that he did have doubts if he wanted a relationship or was ready even as he asked me, but went with it as he liked me a lot and it was what I wanted. He also affirmed that with time, he knows he made the right decision to commit to me.

I share a similar dating philosophy with your wife. I believe in mulligans and I am grateful that my partner and I are able to talk about us – what a joy to find a man who wants to talk about the relationship! – and I have no desire to punish him for his honesty in any way or to use it to guilt him. His recent affirmation to the commitment also made me reassured. In fact, he has ticked all the boxes that you mentioned in what a man should do for his girlfriend. He is by no means an alpha Marlboro guy and my younger self would have found flaws in him, but my older self agrees with your philosophy in being with the man who treats you well and wants to be with you.

However, I have some niggling fears over his admission that he wasn’t ready when he asked me to be his girlfriend, and that he had doubts even after he had asked me during the early days. I would love to hear your opinion on whether this is a red flag. From my perspective, I appreciate his desire to be honest with me and have no wish to punish him for it. But you have more experience and insight, and I’m sure myself and other female readers would benefit from your thoughts on this.


Think about the relationships where you had no doubts whatsoever.

You “just knew” he was your “soulmate” and you’d be together forever.

What happened to ALL those relationships?

You got it! They fell apart. So much for “just knowing.”

I don’t know how long you’ve been with your boyfriend, Margaret.

But if he’s treating you well and is talking about a future with you, it doesn’t matter at all if he had doubts at the beginning.

Doubts are just signs that you’re seeing things clearly and can tell your partner’s flaws.

While it’s no fun to have doubts, they’re necessary before taking the plunge into marriage, lest you end up like the couples who “just knew” but were mistaken.

Doubts are just signs that you’re seeing things clearly and can tell your partner’s flaws.

I famously had doubts about proposing to my wife.

I told my friends.
I told my therapist.
I told Dr. Pat Allen — who told me to dump my wife or I’d end up cheating on her. I even told my girlfriend directly — two weeks before I proposed — that I wasn’t sure what I was going to do, but I knew I had to do it soon because she was 38.

Should she have been scared? Well, yes and no.

Yes, I was admitting that it was in the realm of possibility that we might not get married.

No, there was nothing to be afraid of because my decision was out of her hands.

Many women would have freaked out, dumped me, or tried to extract an ultimatum.

My future wife didn’t.

She knew I was a serious, relationship-oriented man who desired marriage and kids.

She knew I never lied.

And after having a first husband who cheated on her, it was refreshing to be with an honest guy who articulated all of his thoughts and emotions, however painful they might be.

If you’re NOT afraid of making a mistake, you’re not thinking very clearly.

Thus, she put her faith in me that I would come to a conclusion in my own time — despite my admitted reservations about spending the rest of my life with one person.

(Again, if you’re NOT afraid of making a mistake, you’re not thinking very clearly.)

I’m sure it was hard for my wife when I was deciding whether to step up or step out.

But she’s a smart woman with unparalleled people skills and a deep understanding of men.

She knew that if she wanted me to propose, getting nervous wouldn’t help, talking about “us” wouldn’t help, and grilling me wouldn’t help.

She just had to continue to do what she had done for sixteen months before that — be the best girlfriend I’d ever had, accept me as I was, and become indispensable to my happiness.

That’s why she’s my wife instead of Date #301.

So, my friend, allow your man to tell you the truth without punishing him for it. He’ll feel safe that he can be himself with you. You’ll be the only woman who ever let him be honest without flipping out on him. And that’s why he’ll stay with you above all others.

Good luck.

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  1. 41

    Ah, there are to minor things that struckd me with this blog post.

    1. Being honest is good. You should be honest but bringing your girlfriend pain is hardly what a good man does. Deal with your doubts at the doctor’s office, with your therapist  or even your priest but don’t ever utter these words; “I’m not sure about you”. It’s not lovin and how’s it going to make her feel romantic towards him? Apperently it doesn’t and that’s why she’s asking a relationship coach for advice.

    2. I think she is the one who has doubts. Doubts about is this man going to cheris and adore her the way she wants and needs. Is she going to get trapped into a conviniance relationship with a guy who feels she’s good enough because he’s tired of dating, and doesn’t want to be alone. The truth is, she doesn’t knocks his socks off and that’s what he knows deep down inside.

    My advace, since she’s already in a committed relationship with him, work on the desireability factor; talk less about feelings, explore something new and exiting for herself; like cooking, learning a new language, take a trip with friends. Be independent but soft and feminine and let him put in the effort with initiating texts, calls, outings and plans. Make her life full without him and he’ll will crave to be in it.

  2. 42

    Hi Jeremy,

    I just wanted to put in my 2 cents on one snippet:

    “Men seem to want a private clubhouse that women aren’t in, so that they can call it masculine and perceive it as different than what women are.   And more and more such a thing does not exist.”

    IMO it’s a shame that those male only groups / clubs are pretty much a thing of the past. I’m not sure why anyone would take issue with men having their own groups where women aren’t allowed. If those women are interested in a certain group, club, or activity, they should form their own women’s only group.

    I know the boy scouts have recently had some controversy over whether or not girls should be allowed. Parents of these girls who wanted to join the boy scouts claim that girl scouts are not an option because they don’t do as much camping, etc. There are other alternatives for girls who want to camp. There is already a group that is open to both boys and girls called adventure scouting.

    1. 42.1

      Men’s only club are a problem because they are not just a glorified therapy support groups as some would have us believe. They are places where career and business opportunities are shared and if women are not there, they are missing out, never even learning of those opportunities and wondering why they are failing to get more clients, close more deals, or are never invited on that awesome startup investment opportunity that the guys discussed in a “men only” environment. Men’s only clubs must go..

      women’s only clubs are, in my view, completely useless and honestly should go too. There should be no double-standard.

  3. 43


    The thing about having a men’s only club is that it is considered discrimination against women, while a women’s only club is considered empowering and a place for women to share their issues without the prying ear of men.

    My father was a part of a men’s only club in the 1960s and he loved it. Nowadays if a man tries to start a social club with men only, the organization will be sued by the ACLU and promptly closed.

    I remember when I was in my late 20’s I worked at a restaurant owned by a man from North Africa. It was staffed by men only. We would sit around after the place closed and drink mint tea and smoke apple tobacco out of a huge pipe that we all shared. We talked about women, business and politics in a mix of Arabic, French and English. My girlfriend at the time wanted to come and be a part of this scene. I said no. She tried to convince me to let her come, but I refused. This was my space to be with men only and it fed my soul like nothing else. I also knew we would all act differently if she was there. Eventually the owner of the restaurant suggested that my girlfriend go spend time with his wife when we men were together and she could have some “woman” time with her. The place went out of business and I missed the male camaraderie more than the money I made there.



    1. 43.1


      “The thing about having a men’s only club is that it is considered discrimination against women, while a women’s only club is considered empowering and a place for women to share their issues without the prying ear of men”.

      Yes, and I think that’s an extremely unfortunate double standard that needs to change.

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