The Art of Conversation For Inarticulate Guys

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Some guys are natural charmers. They present themselves in a charismatic manner, and never fail to leave a good impression. These are the individuals who have an ability to strike up conversations exceedingly easily, and remedy awkward turns and lulls in interactions without breaking a sweat. However, not every one of us is that gifted at conversation – for the inarticulate guys among us, fret not, here are some tips to help you out!



Conversation starters

Breaking the ice is often the most nerve-inducing part – you worry about making a good impression (which will be half the battle won!), and not having her shut you down immediately. Unfortunately, the responses to your conversation starters will vary from girl to girl, but here are some tried-and-tested tips to ensure that you don’t get kicked to the curb immediately!

1. Be friendly



While this seems intuitive, you would be surprised at the number of guys out there who genuinely think that putting a girl down at the start of a conversation is the way to eventually win her heart. The theory behind this is that when the girl realises that you don’t seem too fond of her, she’ll try even harder to impress you, and be extra appreciative of every compliment or kind gesture that comes her way. However, most girls know their worth, and they won’t put up with this, so steer clear of it! We recommend being jovial and courteous instead.

2. Ask questions

There’s a really fine balance to this: too many questions and you come across as probing and annoying, too few questions and the conversation might flop. Try and make this a natural process, for example, you ask a question, listen to her response, and then craft your response according to something she said, or reply with your own view on the question!

Don’t worry about follow-up questions, just let the conversation flow. The girl you’re trying to start a conversation with will do her part to keep the conversation going as well. And: this should go without saying, but I’ll mention it nevertheless – stay away from sensitive questions such as questions about weight, exes and the like.

Continuing the conversation


You now have an advantage on your side: you’ve already made contact, so you don’t have to worry about your first impression anymore. The tips for continuing a conversation are all very generic, but the key is to remain interesting! People will always tell you to be yourself, but here’s where you have to present the best parts of yourself, before you really get to know her and the conversation flows easily and freely between the two of you. Talk to her about your unique experiences, ask her about hers, and discuss common interests!

Conversations tend to conclude themselves when both of you decide to retreat for the night; it’s often difficult to pick these conversations back up next morning. While the good morning text may appear to be sweet, it might come across as an assertion of familiarity and make her less willing to talk to you, especially if you already seem like you’re really interested in her – this may end up getting her to back off in order to not lead you on.

A much more casual alternative to the good morning text would be replying to her message announcing that she’s going to go to bed the next morning, apologising for the late reply. However, do not try this too often! Maybe a few times in the beginning stages of your conversation is fine, but if you have to constantly rely on this to maintain a conversation, you may simply appear flaky. If both of you have only been conversing online, do ask her to grab a casual lunch or dinner with you and a few other mutual friends, so you’ll be able to seek more common topics in real life!

Rejuvenating a past conversation


I’m fairly sure we’ve all tried this method: you text a person after a prolonged period of radio silence about something interesting, and then pretend the message was meant for someone else. See, the problem with clichés is that everyone knows about them. If you haven’t spoken to someone in a while but would like to rekindle a conversation, just ask them about their life and any new occurrences in it! (Bonus: if she now has a boyfriend, here’s when she’s likely to tell you, since that would be considered a major new development in her life.)

Ultimately, just remember to be genuine and sincere! It won’t help your case if your interaction comes across as contrived. Keep in mind that your conversations should be conducted with the intention of getting to know her better or wanting to just be friends, rather than with the final goal of a relationship in mind, so that you won’t feel too stressed and your conversation won’t veer into artifice or morph into mere niceties, but be intrinsically rewarding and fulfilling.


LunchClick is Singapore’s first female-centric dating app, developed by the dating experts behind the Lunch Actually Group, the biggest dating agency in South East Asia with over 10 years of proven track record. LunchClick is perfect for serious daters and singles looking to find love – we’re SDN (Social Development Network) accredited, and we manually approve all profiles to ensure that you only meet genuine & quality singles. No swiping, no chatting, just offline dates! What are you waiting for? Download the app on the Play Store or App Store today!

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