Dear Love Doctor

When Do I Finally Let Her Go?

Why not send former Kingston-resident Love Doctor your relationship queries? Use the form to submit your question(s).


My relationship has festered for the past two years and we are more like kissing cousins without the kissing following an amazing initial 12 months.

We go out regularly to music events, and I visit her for meals, but I’m not in her heart and I’m not in her long-term plans.

The excitement faded for both of us. We don’t even hold hands in public, nor behind closed doors. I’ve put out so many olive branches to no avail, but our romance has totally died.


I’m in my 50s and want romance? How do I end it without hurting her?
Love Doctor MontiRobert, St. Thomas


Love Doctor’s Answer:

Relationships will always be a rollercoaster ride, but it sounds as though you two fell off the ride two years ago and have failed to jump back on.

It definitely sounds as though any romance has well and truly died a death. It’s not worth trying to rekindle as you are in a doomed relationship.

She cannot be oblivious to the fact that you two are going through the motions as friends, and I would be so bold as to suggest that at least one of you has been looking out for an upgrade for sometime.

Maybe the reason that your romance ground to a sudden halt is because she’s seeing someone else, but hasn’t got the heart to tell you. If that was the case then she would let everything drift, and hope for you to vanish in due course.

Either you are resilient, very thick-skinned or bored to still be hanging around with someone two years after the romance evaporated. On the other hand you may discover that she’s going through “the change”, which accounts for this distant behaviour for the past couple of years.

The more time that you spend time involved with her, the more time you are missing out from being out ‘n’ about with the right lady. You shouldn’t, at any age, be expected to go through the motions like this. It’s not fair on either of you.


You’re in your 50s, so it’s never too late to try to find that someone special to settle down with.

My advice is to start gradually seeing less of her. I urge you to give her two weeks without you, which could jolt her to realise that she’s missing you or it will reiterate the fact that your relationship has been doomed for some considerable time.

After your two-week break, then this is the time for you to have a talk in a neutral venue in public. This is when you can spring it on her that she’s no longer making you happy and explain that you’re upset as you don’t appear to be in her long-term plans.

Do reiterate that although you value her as a friend, you are looking to be involved with a lady romantically and that your current scenario is not cutting the mustard. You really won’t want to backtrack from this mistake of staying with her for so long.

From the little information you’ve given me, then in all reality I would expect her to be delighted to hear this from you. It sounds like you may have been a burden on her in terms of how to break things off.

It should be straightforward enough for you two to agree to remain friends, keep in touch and go to more music events together. That’s the sugar-coated version though, whereas realistically you’ll drift apart and probably only make polite contact for each other’s birthday and at Christmas time.

Be the man, take the bull by the horns and tell her how you feel and what you want. This is the only way forward with any relationship that’s lost its fizz, and it will be a blessed relief for her as much as you to finally draw a line under this seemingly time-wasting that’s been occurring for so long.

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