How To Tell Someone You’re Dating That You Don’t Want To Go Out Again

7 May 2013
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*Stacie’s Top 5 Considerations*

Consideration #1: To communicate or not to communicate

Whether you’ve gone out on one date or three (or perhaps you haven’t even made it to the first date but have had some form of communication) it is always difficult to know how to proceed when you decide you no longer wish to pursue someone romantically.

Men get a bad rep for being “assholes” when they don’t call or text and seemingly “disappear”, however, women are just as guilty of doing the same. The difference is – most men don’t sit around talking about it with their buddies, so it doesn’t seem to be as well-documented.

In most cases, the Houdini act is one’s attempt at not hurting the other person’s feelings…there is rarely any malice behind it (although the women I’ve spoken with – and some men – allow their imaginations to think otherwise). Often, too, it has nothing to do with YOU and everything to do with THEM. Never profess to know what is going on in someone else’s life.

While I don’t believe in dating “rules”, per se, I do believe that communicating – something – is better than no communication at all.


Consideration #2: What form of communication to use

I’m an old-fashioned kinda of gal (while simultaneously being a texting whore – I’m a bit of a walking contradiction)…so I always prefer the phone (or face-to-face) for important conversations. That said, it really depends on how long you’ve been seeing this person and what the nature of your communication has been like – i.e. what precedents have already been set?

The general “rule of thumb” – bearing in mind that I don’t typically subscribe to rules – to be used as a guideline only, is as follows:

Zero to two dates:  text or e-mail is fine
Two to four dates:  E-mail or phone
Five dates or more:  Phone or face-to-face

Consideration # 3: To be honest or to spare feelings (often – but not always – mutually exclusive)

I strongly believe – whether in dating, or otherwise – that honesty is the best policy and that the worst truth is better than the best lie. How many times have you gone on a date with someone who you were interested in, never to hear back from them again?  Or, to have them feed you what you know to be b.s. lines, like “It’s not you, it’s me”, “I’m just really busy with work right now”, “I’m not ready for a relationship”, “I’ll call you soon – when *everything* calms down a bit”…and the list goes on.  Even if it were to sting a little bit, wouldn’t you have preferred to know the actual reason why? What if that feedback could help you improve your dating success with other suitors?

I coach and encourage my clients to tell the truth – sometimes including brutal, yet well-packaged, honesty. If you don’t want to see the person again because you found that the conversation was lacking – tell them that. It is all in the delivery. Not everyone will appreciate your candor or feedback, however, MANY will, and those people will go on to become better, more informed and more successful daters. Think of it as contributing to the greater good of increasing the frequency and volume with which romantic connections are formed.

If we all keep running around sugar-coating and sparing feelings, nobody in the dating community learns anything – about themselves, the process, or others’ perception of them.  Instead, we keep sending each other back into the dating pool thinking “well, it had nothing to do with me…obviously THEIR LOSS”…which might be true, but we are not doing each other (the collective dating community) any favours.

Please go to and read the blog called “Match Made On Palmerston Avenue”. It is meant to be a good example of how the smallest detail could send a potential love connection off the rails and how the benefit of perspective, insight, having an open mind, and even enlisting the help of an objective, experienced third party, can salvage potentially lost/missed opportunities.


Consideration #4: What to say and how to say it

What to say: the truth.
How to say it: diplomatically.
That is the simplest approach.

Whatever you do though – please do not say: “I just didn’t feel any chemistry”. While that might be true, it’s the biggest cop-out and doesn’t help anyone. Before you decide to stop seeing someone, get real with yourself. Figure out the actual reason. If you’re not physically attracted to them, tell them that, nicely.  It is likely something they have felt toward other people they’ve dated, so it’s something they can relate to while being less vague than “no chemistry”.  Nobody likes to hear that someone else finds them less than attractive, but – over time, if not immediately – it’s something most of us can get our heads around.

If you felt the conversation was awkward…say so. If you were put-off by the fact that they were late, or cancelled twice, or whatever the case may be – say so.

Whatever you say – in order to remain diplomatic, here are some general tips:
1) Use “I” rather than “you” whenever possible
2) Maintain their self-esteem. For example, instead of saying: I thought it was rude that you expected me to split the cheque with you and found you to be quite cheap, say: I’m sure that you have the ability to be generous but I was not prepared to share the bill and was caught off guard. In other words, try to avoid any character assassination and focus solely on the particular circumstances, rather than the person.
3) Share accountability where appropriate. So, instead of saying: You didn’t really talk that much and I felt like I had to keep the conversation going, say: I know first dates are often uncomfortable, and I was nervous too (if you were) so I found the conversation difficult to maintain and would’ve found it helpful if you had made more of an effort to initiate conversation or contribute more than one-word answers.
4) Compliment them/say something positive (only if you can do so while being genuine). For example, in closing, say something like: I did enjoy our time together. I particularly liked the story you told me about __________, or the part of the evening where we ______________ and would definitely recommend you to a friend (if you would)…I just don’t believe that we’re a match, and that’s OK. That is the purpose of dating. I wish you well and thanks again for a lovely evening/day/few dates/etc.


Consideration # 5: What to expect in response
a) Nothing
b) A simple “Thank you, I had a nice time too”…which is usually an indication that the feeling was mutual, and is the classiest response
c) “Thank you, I had a nice time too and was feeling the same way”.  Mutual.  Classy.  Honest.
d) An expression of disappointment with a subtle plea for another chance. This is where people may surprise you, or where you may consider opening your mind a bit more, enough to give them another chance.
e) Anger. Where/if this is the response – remember that this is their issue, not yours – especially if you followed the tips on how to package the message with diplomacy, tact and sensitivity. In these cases, just be thankful that you dodged a bullet.