There are a wide variety of what could be considered awkward conversations that couples and soon-to-be couples can have. In my opinion the sooner you have them, the more likelihood the relationship will work out. What makes them awkward, of course, is complicated. It depends on the people in the relationship, what they want, their individual communication skills, and communication compatibility as a couple.
Let’s start with this one.
You are a bit older and have a crystal clear image of what you are hoping for in a relationship. You might begin the awkward conversations at the outset —which is what makes them awkward. Telling someone on the first (maybe 2nd) date that you are looking for a partnership relationship (maybe you want kids), rather than a happy hookup, might be awkward. And it is required to avoid future distress. Most of us wait, because “I can’t bring that up in the first date”! And then it just becomes more and more awkward. You get along and you have no idea what this new(er) person wants in relationships and life. Find relief for all parties and say what you know as soon as you know it. At least you will be clear you are going for the same thing and have confidence there is a reason to move forward. Then you can have fun figuring out if you are a perfect match.
Once you are in a relationship consider having the conversation about your past sexual history. Name partners, and even include what the relationship was like —what you enjoyed and what you did not. This might be awkward, and likely important over time and here’s why. Maybe your current partner is in the same community of friends with your past partners. You want to be the person who lets your partner know. If previous relationships didn’t end well, and you are invited to things you don’t want to go to, that is probably not the time to tell your partner. And I encourage you not to lie to your partners about anything. If your partner can’t handle your life, then they aren’t for you. Period. No matter how much you like them.
Having this conversation will also give you some great information. If your partner consistently finds fault with his/her past partners —that they (the other person) are the reason for the relationship not working out, this is a red flag. If your partner is holding a grudge against one or more previous partners, then it is another red flag. Unless he/she has done or is doing some serious self-reflection work, you will be the star of the next bad story he/she tells.
Some other possibly awkward conversations include talking about how you feel about his/her family (or they yours). What about this scenario: He/she absolutely loves their family and every Sunday are at the parents’ house no matter what. His/her mom and you just don’t see eye to eye, so-to-speak. You are fairly certain Mom is not going to warm up to you, and possibly you have little interest making it happen because you don’t want to warm up to her. This could be challenging, couldn’t it? Certainly awkward. The most important thing here is not whether or not to have the conversation, it is how you have it. Choose your words carefully.
Same caution applies if something similar is happening with non-mutual friends. If his best friend makes a pass at you, or other friends are less than welcoming, then this could be seriously awkward to talk about. Have the conversation, choose your words carefully, and be prepared for any outcome.
How about these?
How do you bring up bad breath, body odor or stinky feet? Awkward. The relationship is super-great. Laughing a lot, deep conversations and shared world views. You partner just stinks. Before you bring it up, consider if there are other ways you might impact the odor. Different laundry detergent, tooth brushing games, foot massages with essential oils, perhaps? If not, then be sweet and be direct. Acknowledge how difficult it is to bring it up, and then just do.
Your relationship is awesome. Your partner is fun, funny, self-reliant and kind. Honest and communicative. However, sex isn’t so great. There are things you would like and your partner hasn’t offered once. And it’s been a year! This is an awkward conversation to have. Sex seems to be so difficult to talk about. We must change that. For lots of reasons. If you are going to have sex, then talking about what you like, what you don’t like - specifically and clearly - is a conversation you want to have —as part of your sex play! If you (and your partner) have been shy to have this one, possibly suggest some reading together? Find a book about sex, sensuality and/or intimacy and read it together. Name your parts. Say the embarrassing words. And get to practicing.
Finally, the ultimate awkward conversation.
You no longer want to be in the relationship. Or even more difficult, you aren’t sure. Things aren’t going the way you want. You haven’t been enjoying your time together. You are confused about whether to stay or go. When things aren’t horrible, when that “deal-breaker thing” hasn’t happened, just a sense of disappointment or dissatisfaction. This is the challenging conversation.
Somehow you think that because you no longer want to be in a partner relationship with someone, it means you are telling them that something is wrong with them. It isn’t true. Maybe you like them lots, have fun together in many ways. There are just certain needs you want to get met in a partner relationship, and your current partner isn’t into what you are in the same way.
Putting off this conversation likely lengthens the amount of time you will feel awkward. Having the conversation will offer you some clarity at very least, possibly understanding —if your partner can accept and discuss the concerns, and maybe some deeper connection. Meaning you are more connected about what to do, even if you (and/or both of you) might feel sad about the choices you are making.
My hope (and my work) is for couples make these awkward and challenging decisions together.