8 Tips for Broaching Awkward Conversations With Your Date

11 Jan

Are you in the early stages of dating exclusively? Do you have something you need to share with them, but you’re dreading it? No relationship can work without residing in a place of truth.

couple having awkward conversation

Hiding, being ambiguous, shelving, storing, avoiding, are all things that are a recipe for distrust. It’s quite possible that with all good intentions you may think it’s wise to not divulge or discuss, but ultimately if it’s important, it’s always going to be there. If the awkward subject emerges inadvertently, from the wrong source, or in the heat of the moment, it could prove to be irreparably damaging.

To begin you have to have the courage to approach your relationship from a place of vulnerability. That doesn’t mean being weak, compliant or a victim, but conversely having the courage to speak truth and being OK with the consequences. This also doesn’t mean nit picking, being over exposed, or hard, but ask yourself, wouldn’t you rather know the truth?

Here are our 8 top tips to help you negotiate what can often feel like a minefield:

  1. Prepare for difficult conversations

If it’s important then it’s equally important to invest time in preparation, not just thinking about it. Often it helps to write down what you are thinking and starting with focusing in on what the headline or topic is will help you get clarity. If the conversation were to do well, what or how would you like it to turn out in the end? Examining these things helps you to arrange your thoughts, specifics and removes what’s irrelevant and unnecessary.

  1. Don’t delay if it’s really important

If you are afraid of the subject, or it feels like something terribly important you can’t shake off, or carry on without discussing, then don’t delay. It’s essential to get it out on the table honestly and clearly, rather than pretending to yourself that it might go away, or never come again, when you know in your heart it will. If it’s critical to the long-term success of a fledgling relationship, then delaying is only delaying the inevitable. Avoidance just doesn’t work, that’s just a delay mechanism.

  1. Choose discomfort over resentment

Brené Brown is the known expert on the subject of vulnerability and shame, and she is known to quote these words when talking about setting boundaries and avoiding people pleasing when our yes really means no, or vice versa. It really takes practise to get comfortable with leaning into discomfort, but what better time to start than early in a relationship, as it will often reveal immediately what kind of person you are interacting with and considering as a life partner.

  1. Time and place

Choosing the time and place is an important element to consider. If we decide to dive into an awkward conversation when we or the other person are tired, rushed or unfocused, that could be a recipe for further awkwardness. Go for a walk together, make sure you are in privacy and not being overheard by strangers. Not 5 minutes before you get out of a cab, not at the end of a mobile call when you know you need to hang up immediately. Give the conversation and the person space. If you are unsure, think about what you would want if you were on the receiving end.

  1. In-person with eye contact

In a digital age, there is nothing worse than hiding behind a text or an email. Not to mention how unless you are phenomenally adept at composing messages, there is always the possibility of misinterpretation of what you are saying and tone of delivery. Be brave, do it in-person, with full eye contact, so that the other party can hear and see the somatic and feel your intention. Don’t think FaceTime or WhatsApp is the great alternative, it’s not, invest the time and if it’s awkward or important have the courage to be present.

  1. The greatest gift is to listen

Whatever you have to share has been known by you possibly for some time. You know everything about it, they don’t. Breathe, pause, be present, and allow them to question. Listen with enthusiasm so you don’t just hear them speaking, but be in a place where you really want to know what they are thinking. It’s so easy to be preparing what we want to say when someone else is speaking, usually in defence, but try asking “What else would you like to know or understand?”. Have the courage to ask and not just tell.

  1. Start as you mean to go on

If this is a new relationship and you are keen for it to work, now is the time to lean into honest conversations and be prepared to go into awkward territory. If you tell your partner how you feel about exposing yourself, but how much truth really matters to you, it displays the strong kind of vulnerability. It acts as a real time rehearsal of how you want to go on in the relationship. If you start now with never going to bed or parting without letting go of bad feelings, you’re doing brilliantly in creating a foundation for relationship success.

  1. No subject should be taboo

The awkward conversation could be about anything at all, financial status, family dynamics, relationship ‘baggage’, medical conditions, or psychological insecurities. While you clearly don’t want to come across to any new partner as a car crash human being, or such a mess they will run screaming for the hills, if anything is a relationship or trust blocker for you, then it’s probably the awkward conversation you need to have. It’s not going anywhere anytime soon, and if it’s important enough to ensure the relationship will stay the course, then at the appropriate point, when you know it feels right, you will have to go there.

When you lean in and do the work, you will ultimately get into a nice rhythm of good, honest conversations, in the right context, framed well, and delivered with love. Your sense of trust will grow with the right person, both of you leading from a place of deep truth and honesty in which your love can only flourish and bond. Start as you mean to go on, and if in doubt, don’t.

At Vida we specialise in the psychology of relationships and coaching people to make a success of romantic human interactions that lead to successful and lasting life partnership, get in touch for a chat to discuss how we can help you navigate your dating life.

by Rachel Vida MacLynn

Founder & CEO

Rachel Vida MacLynn is reputed as being a world-leading matchmaking and dating expert. Registered as a Chartered Psychologist with the British Psychological Society, Rachel advocates a professional matchmaking approach based on psychological principles and professional consultation.More by this author

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