5 Awkward Conversations with the Opposite Sex


Don’t know what to say? Don’t know how to say it? Here are five awkward conversations with the opposite sex…

…that probably shouldn’t be.

Four Holidays
Source: New Line

Over the last few weeks I got to catch up with a few friends I don’t always get to see. I try my best to stay in touch with most of the people in my world. Obviously you can’t be super close with everyone, but I still like to keep the connections open and the ties relatively strong. And Easter time is usually the time where even the most socially awkward of us make a bigger effort.

I was talking to a few people who were saying they find it hard sometimes to cross the gender boundary when it comes to conversation. They were pretty frank about some of the difficulties when it comes to talking to the men and the women in their world. It got me thinking of how many times we find relating to each other quite difficult, whether it’s with a member of the opposite gender we’ve just met, and even sometimes if we’ve known them for a long time.

I appreciated their honesty. You know, a lot of us find ourselves in that boat at one point or another, for whatever reason.

So I thought it’d be worth taking a look at 5 different situations where we find this awkwardness. Not claiming to be an expert on them or anything like that, I just like talking about the things that all of us are often thinking, but rarely actually give voice to. Keen to hear your thoughts on these ones too.

So here are 5 awkward conversations with the opposite sex… that probably don’t have to be.

#1: Hello

That famous scene in Jerry Maguire makes us believe the opening words to a conversation should let us capture every heart, and yet instead of having them at hello, we sometimes struggle with even starting the conversation.

You know, it would be very easy to get judgmental on this one, but being completely real, many people actually do find talking to a guy or a girl difficult. It’s actually a big struggle out there.

For some of us, we just haven’t had a lot of exposure to talking to the opposite sex. Sometimes people went to single-gender schools, didn’t have brothers or sisters, or had some struggles with that gender parent growing up. But I think there’s a bit more to it when we’re feeling this way.

I think our struggles with hello actually say a lot more about us than they do the other person. It’s usually more about our insecurity or our past experiences. Insecurity in that we don’t know how we’ll be perceived or accepted. Past experiences in that you may have had men or women cut you down or really hurt you before, and so to avoid even going down that road, the idea of even friendship or acquaintance completely turns you off because this person probably has an agenda, right? Maybe they do. Maybe they don’t. And so when that member of the opposite sex is present, you lock up and don’t know what to say.

I think we’ve got to even see beyond the gender boundaries that you’re talking to a person. A person with feelings and needs, just like you. No need to be weird about it. Just treat them like a person and the rest will be much easier.

#2: What do we talk about?

Okay, so you’ve got the greeting down pat. You can say hello to him, you can make the small talk with her. But uh oh, some of your mutual friends have walked off, or this person has started talking to you while there’s no one else around.

Now what?

It’s funny how much we struggle to make conversation today. Maybe it’s because conversation requires us to use more than 140 characters to describe what we’re thinking or how we’re feeling. Maybe it’s because we don’t view it as important.

Or I think more commonly, we just don’t know what to talk about.

I think if you’re having this problem with the opposite sex, you probably just actually have this problem having meaningful conversation in general. It’s probably magnified with the opposite sex cause you don’t know them as well whereas in your friendships you’re already used to a certain level of exposure.

Men and women are definitely different, with different tones of voice and approaches to storytelling that can play a factor in things. But what can be awkward is when we just see the person’s gender instead of the person. Sure she may be a woman, but she doesn’t fit into your primary school stereotype of hair and make-up (or maybe she does), and she actually wants to talk about the cricket or the UFC. Likewise, maybe the guy’s not just into working out and muscle cars, maybe he has interests of his own.

The fastest way to end a conversation is to stop asking or answering questions. It’s usually at the point where one or both people stop asking or answering questions that the feeling of awkward sets in. It’s amazing what you might find out about someone just by continuing to be open and interested.

#3: I like you

Remember the high school days where people would talk about their crushes? Do they like her, or do they like like her? They would tell their best friends who would tell the other person’s best friends. Oh the juvenile days.

In some ways, we don’t always actually move past our childish behaviour around affection.

I think the main reason is because it usually involves the biggest dreams of your heart. Even if you’re not madly in love with the person, the notion of broaching “that direction” with them may feel like a massive deal because of all the long-term associated decisions. I think that’s also the reason we respond awkwardly to this conversation many times – we think it means they want to marry us right now.

I think you just need to be really clear about what you want. If you want to explore the relationship, say you want to explore it. If you don’t see a future and you’re absolutely sure about that, say so. If you’re not sure, say so.

Having this conversation, either as the initiator or the recipient, can take a lot of courage, but I think if you’re keeping in mind the person you’re talking to you’ll probably get through it the right way.

And it doesn’t have to be awkward, even if it is sometimes a painful one.

#4: What are we doing?

Ah man. This freaking conversation. No one likes this one. Louie Giglio calls this conversation “DTR” – Define The Relationship. It’s also been jokingly referred to as “Destroy The Relationship”.

You know the one. You’re spending so much time together. You’ve talked on the phone for extended periods. Things are going great. But barely even friends, then somebody bends, unexpectedly. And someone’s heart is getting a bit further ahead. They’re starting to think about those compliments you’ve been giving… do they actually mean more than that? That trust you’re giving me… is that a trust you want to continue to develop? You like spending time with me… does that mean you want to spend more time together? Is there actually some potential here for something more?

Just what are we doing?

This one takes a lot of bravery too. I think this one once again plays on the deeper things of the heart. Because this is such a big and potentially relationship changing conversation (well actually, it pretty much always changes the relationship), we avoid thinking about it. But when the heart gets further ahead, it needs an answer. Should we pull back, or take it to the next level?

This is usually quite an involved conversation to have, but I think we shouldn’t avoid it just because “we’ll feel awkward” or “it’ll be awkward afterwards”. What would be worse is never having this conversation and the explosion that happens when someone ends up with someone else.

And even when you’re in a defined relationship, this conversation is more about where exactly we are going together. We used to have dreams together – what happened to them? We used to be so much more involved in each other’s lives – why isn’t that the case any more?

Be brave and take the plunge.

#5: I was wrong

We never like admitting we were wrong, especially with the opposite sex. Not entirely sure why it makes it so much more potentially awkward, but sometimes it does.

I think it takes a real man or a real woman to fess up to their mistakes. To take responsibility for their own actions. So often though, we let our pride destroy what could be really great.

We say something hurtful, but we feel justified about it. We made an assumption that wasn’t correct, but we were so sure of ourselves. We thought we knew what we wanted, but we changed our mind.

Pride is the original destroyer of relationship. Let’s make sure it doesn’t destroy any of our other relationships, with friends or otherwise.

I wonder if you’ve had any of these conversations before. I wonder if you find it awkward even saying hello, or maybe you’re in a great relationship but pride’s sneaking it’s head in and making things difficult. Wherever we find ourselves, I think openness and honesty will always win the day.

How about you? What do you think on awkward conversations?


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