Posted in Dating / Relationships

Is there ever a right time?

I had a bit of an intense conversation the other night with Miss X about life and love and our collective lack of relationship experience. We’re both going through the same sorts of feelings right now: we both feel unattractive to the opposite sex, we’re both convinced of our ‘undateable’ status because we are both such complicated creatures with demons to battle and naturally, assuming that we must be weird or abnormal.

Of course I did what any friend would do; I told her that she has some amazing qualities, that she has a good brain, is great company with a cracking sense of humour and, of course, that she is good looking. None of these things are untrue so I wasn’t just telling her to make her feel better (I guess what I was trying to tell her is that she has qualities that are attractive to me regardless of anybody else). She is one of the most intelligent people I’ve ever known; she is great company; we have a lot in common and I think she is beautiful.

In the middle of all of this I wanted desperately to tell her just how attracted to her I am, how she is my type and that I’d always had a slight crush on her and that meeting her did not change that; if anything it enhanced it or at least made it feel more real.

I bottled it; I couldn’t bring myself to do it. The time does not feel right because we are both muddled emotionally. I want to have moved on from my old life in some small way and – at least – not living in the same house as my estranged wife.

I also have demons in my life that have to be beaten before I can think about accepting anybody else into it; particularly the emotional investment of a romantic or sexual relationship. I clearly a break from the past before I can move into the future.

I also have trust issues relating to my wife cheating on me. I’m concerned that if I meet somebody else I might have difficulty in trusting them not to trade me in for somebody less complicted, better looking, more successful or as happened in my case, a nice guy dumped for a bad boy. While I have such chronic self-doubts, I can’t think about any kind of relationship.

Most of all I want to tell her in person and all the perils or advantages that entails. She is my friend, I care about her and I want to be able to look her in the eye. I know that there remains the risk that somebody else might pip me to the post but that is a risk I have to take right now.

And then I got to thinking about whether there truly is a right time to tell a good friend that you desire to be more than their friend. I also started to wonder whether I’m just using that as an excuse to keep delaying the inevitable – I will have to tell her one day.

So when is the right time? Did I do the right thing in holding back despite that she was bemoaning the lack of male attention throughout her adult life? Was I right to play it cool and tell her, as I did, that as a straight male I cannot comprehend why somebody with her qualities isn’t spoilt for choice?



I go by the name of Frank Speaking. My blog "In the Mind of Men" (former name Chin Up, Chest High) started out as a chronicle of my mental health recovery. Now it is a forum where I discuss issues related to male mental health.

7 thoughts on “Is there ever a right time?

      1. Don’t rush things, true. However, recognizing that you have a wish to rush, for this girl, is a good sign toward moving forward. If you feel she would be receptive to your interests then, leap.

        1. Thank you for your advice. As we live on different continents it may be some time before we meet again so I have plenty of time – who know if I arrange to fly out again next year I may feel ready by then

          She has given the impression in general conversation that long-distance relationships are not a problem for her, so that is not a concern for me,

  1. Just tell her. You only live once. You never know, she might be harbouring the same feelings, and within a couple of weeks you could be moving across the world to live with her. Bingo! New house, new life, new woman, and plenty of distance from your old baggage.

    And if she says she doesn’t feel the same way, well, at least you tried. It’s better to try and fail than never try at all. Realistically, given that your friendship is long distance anyway, would it really spoil it? If she rejected you romantically, wouldn’t the friendship continue anyway?

    I understand that you need to work through your past, but stop allowing it to be an excuse – or it will hold you back forever.

    All the best, whatever you decide.

    1. I fully intend to grab the bull by the horns and tell her… I just don’t think that the time to do it is now.

      Thanks for the kick up the backside, I do need them sometimes 😉

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Google+ photo

You are commenting using your Google+ account. Log Out /  Change )

Twitter picture

You are commenting using your Twitter account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )


Connecting to %s