August 5, 2024

Written by

Sarah Kyle

3 Must-dos for Having Hard Conversations When You're Dating

Master the art of handling tough conversations while dating with these 3 must-do tips! Improve your communication skills and build stronger connections effortlessly. Check out our latest blog post!

One of the most challenging things about dating is delivering information that may be hard for the other person to hear. Our tendency is to want to let the other person down easily, so we try to soften the blow by being indirect. I recently worked with Zach, who had gone on several dates with Lee Ann. He really liked her and they had a great time on their first two dates. By date three, he started noticing she was over-drinking and getting a little sloppy by the end of the evening. Instead of opening an uncomfortable dialogue with her and telling her what he was experiencing, he started distancing himself until the contact just fizzled out. 

The thing Zach did well was evaluating goodness of fit. He knew he didn’t want to be in a long-term relationship with someone who abuses alcohol. Rather than thinking Lee Ann might change, he opted to bow out and look for a partner who is a better match. However, because of the newness of the relationship, both Zach and Lee Ann might have been better served by having a conversation about this potentially sensitive topic. He could’ve found out more about her drinking patterns. Is the over-consumption typical for her, or was it a reaction to her nervousness about being on a new date? What is her attachment like to alcohol? If she is normally a big drinker and alcohol is an important part of her life, both of them are better off finding other dating partners. But perhaps there’s some reason she is doing something outside her norm, and she truly wouldn’t mind reining in her drinking. This conversation would give Zach confidence in speaking up about his feelings, and it would likely give Lee Ann some information about how alcohol changes her personality and can potentially impact her relationships.

Here are some tips for discussing the hard stuff:

  1. Begin from a standpoint of genuine curiosity. Don’t jump to conclusions or judgements. Instead, stay open and ask for more information. 
  2. Run everything through these three gates:
    1. Is it true?
    2. Is it kind?
    3. Is it helpful?
  3. Speak from a self-responsible perspective. Let the other person know what you observed and how it affected you.

So how would these things look in the above scenario with Zach and Lee Ann? Zach might begin by asking a question like, “I would love to know more about your relationship with alcohol. What has drinking been like for you?” He could let Lee Ann know how much he enjoyed their first couple of dates, and the specific things he likes about her. Next, he could say what he observed after she had a few drinks; something like, “I noticed by the end of the evening you were starting to be more sarcastic, which was unlike my experience of you before. I’m wondering if this had something to do with the alcohol.” Then he could say what he wants, and see how that matches up. “I’ve found that I’m a better fit with someone who doesn’t drink much and who doesn’t drink often. How do you see that lining up with us?” This gives Lee Ann a chance to evaluate the fit as well, and to make a potentially minor adjustment that would allow the relationship to move forward. If the two are not a match, they both know why and it gives them good information going forward.

The bottom line is, having a hard conversation may be scary or distasteful in the moment, but it’s the kindest thing you can do for yourself and for the person you’re dating! If you’d like help learning more about this, Get Dateable is here for you. Ready to learn more? Check out our Dating Masterclass today and become your best, most dateable self!

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