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Learn These Key Online Dating Conversation Starters

Published: November 19, 2015 | Last Updated: February 28, 2021

You’re wearing a great outfit with killer heels, your makeup, hair and accessories are top notch. You’re looking damn good but you’re feeling edgy, your nerves are jangling; it feels as if about a thousand butterflies are fluttering around in the pit of your stomach. None of this is surprising because, when you think about it, you’re off to spend the evening with a total stranger. But more than that, there’s a lot riding on the meeting – if it goes well, this man could be your future husband, if it goes badly, the first date might well also be the last….end of story. So, no wonder you’re feeling agitated.

One of the main things which catches women out on a first date is their mind goes frustratingly and totally blank…they can’t think of anything to say. Not a thing. Ouch, awkward. So, read on for some suggestions to get you through those tricky moments and keep the talk flowing like a river, giving you a chance to assess whether the guy is worth date #2, even husband material. Keep the conversation prompts up your sleeve to fill up conversational lulls rather than regard them as a script you have to memorize and work through.


Stage #1:Breaking the ice
Just to relax you both (remember he’s probably shaking with nerves too), you could start with some standard open ended questions (ones that he can’t just mumble ‘yes’ or ‘no’ to):

What have you been up to today?
Have you been to this place/area of town before?
Where do you work/live?
Do you like your job?

A few points to remember here:
Avoid rushing nervously through a list of questions, ticking them off as you go. Listen to the answers and follow them up, so it feels like you’re having a conversation rather than an interview. And, don’t get carried away and dominate the conversation. Give him an opportunity to show some interest in you and ask you questions.

Stage #2: The ice has melted

Remember the rule of thumb: boring questions will produce…boring answers (no surprises there!), so, once you’re both feeling at ease, move on swiftly to something a little less predictable, more exciting. This will give you the chance to get below the surface of your date and give you some idea whether you’re sitting opposite Mr Right or not. Having said that, probably best, at this early stage to steer clear of potentially tense subjects like religion or politics but that still leaves plenty of scope for other topics. Oh and try and mix up questions with comments, so your date doesn’t feel he’s being interrogated by a firing squad.

Here are some suggestions:

What’s your all time favorite movie?
What’s the most beautiful place you’ve ever visited?
If you could have a free flight to anywhere in the world, where would it be?
If you won/inherited a million dollars, what would you spend it on?
What’s the scariest/bravest/strangest thing you’ve ever done?
What’s the weirdest food you’ve ever eaten?
What’s your most embarrassing guilty pleasure?

If your date seems to be someone with a good sense of humor who can think outside the box, you may want to try out a kookier line of questioning, for example: if you were an animal which one would it be? If you had to save just one of your friends from a sinking ship, who would it be?

Now at this stage of the date, you’ll have to use your discretion and make a couple of decisions:
I’m guessing you don’t want to waste a lot of time dating, or even worse, falling head over heels in love with a guy who just wants some ‘no strings attached’ fun.

If you’re looking for marriage and babies, you need to know if you have a commitment phobe, an ‘I’m not looking for anything serious at the moment’ kind of guy on your hands. So you may want to get this straightened out right from the start, then you’ll know exactly where you stand. But be careful, you don’t want to frighten the poor guy off and make him think he’s just being used as a sperm donor because your biological clock’s ticking away. You may want to leave this topic altogether for now or you could broach it gently with a lighthearted question like, ‘So where do you see yourself in 2/5/ 10 years time?’ His answer should give you an idea as to whether he’s a playboy or a serious contender in the game of love.

Above all, however desperate you are to get a ring on your finger and a positive pregnancy test, do not, I repeat, do not, let even the slightest hint of this leak out during your first date. If you do, chances are your date will be outta the door before you can say, ‘nice meeting you.’

Stage #3 Ending on a good note

On a first date, it’s generally best to quit while you’re ahead so keep the meeting fairly short and sweet rather than wait until you’ve exhausted every possible conversation topic and you’re both shuffling in your seats, wondering how to get away. So, let’s say it’s all gone well and you’d be more than happy to have a second dose of this cute guy, what should you do? I’d recommend letting him know this without gushing (remember what I said about desperate). Tell him you enjoyed meeting him and pick up on something he said which was funny, interesting, unusual and then say, super casually, ‘you’ve got my phone number haven’t you?’ Cross your fingers and don’t push it any further.

Unfortunately, ladies, there is no manual for foolproof dating, nothing you can follow to the letter. You have to go with the flow and deal with the guy in front of you but hopefully, the above tips will make you feel a little more confident about having a fun, relaxed date. Try not to have too many expectations – he’s bound to fall short of these and do give him the benefit of the doubt. Shyness and nerves – yours and his – can easily convey the wrong impression. Unless he’s quite clearly an absolute ‘no no’, give him a second chance before you ignore his calls and toss him out of your life, like a piece of paper in the trash.

Author: Kristina From EyesOfAWoman.com

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