Tag Archives: first date

10 Great Questions to Ask on a First Date

by Jake McMillan

First Date 1st Date (5)

First dates can be nerve-wracking and awkward at times and even if conversation is free-flowing, it is always good to have some questions in your back pocket just in case there is a stutter in conversation and/or you want to get to know the person a bit better. Internet searches on this subject will bring back a lot of questions to use that are, in reality, not very good as they are trying to be too clever, too relationship-focused or just too lame (e.g. what is your star sign?).

A good question to ask on a first date is one that helps you get to know the other person better in a relaxed manner as well as keeping conversation flowing in an interesting and fun way.

So here are some suggestions of good questions to ask your date:
(note: you don’t need to use all of them, or in any particular order, but do ask them at relevant moments and be ready to answer the question yourself too)

1. What movies do you hate?
Don’t be cynical, asking about movies is really good as it doesn’t seem like a personal question, but actually the movies we love and hate reveal a lot about us. The characters and stories we are drawn to or repulsed by are often quite insightful to our own personalities, our aspirations and our morals. However, if you ask someone what their favourite movie is, they will be put under pressure to say something acceptable and will often say a film they like a lot that is generally perceived to be cool and interesting rather than their actual favourite which is usually a more personal choice.

Asking someone what movies they hate is a much easier and more fun question to answer and can lead very comfortably conversation-wise to movies they enjoy or have seen recently. For example, my answer to this question is ‘Mamma Mia’ and this often leads to great discussion and banter.

2. Who do you admire or look up to?
This seems like a question about someone else, but actually it reveals a lot about the person by highlighting the attributes they have or would like to have themselves. Warning, do not throw this question in willy nilly, make sure it is appropriate/relevant to your conversation or it will seem too obvious you are probing and put the person under pressure.

3. What is your favourite swear word?
I think the more general question of ‘what is your favourite word?’ is a good question, but perhaps more appropriate with friends. On a date, you want to make things interesting, fun and maybe a little bit provocative now and again. How someone answers this question can also be very revealing. Someone more straight-laced may struggle with it, but someone fun and free will get stuck into this question.

My answer to this question is ‘bollocks’, there is just something great about how you can say it. If you have been having flirty conversation, you might answer, for example, by saying that you like a nice ‘fuck’ now and again. Use of the c-bomb should be cautioned, however.

First Date

4. Are your friends with mostly men or women?
This is a good lead into them talking about their friends and the people that are important to them. Also, it can lead to the person talking about how their own gender perceives them. You can follow up with, ‘Who is your best friend?’, ‘Can men and women every really be friends?’. Yes, is the answer to the latter.

5. Do you prefer dogs or cats?
This does seem like a very average mundane/lame question to ask, but it can be a great conversation starter. Their answer actually doesn’t really matter as if you have different views then you can have a fun discussion about why which animal is best. If someone doesn’t like either, then this again reveals something about them. If they do have a preference, then this will lead them onto talking about a favourite pet and this is a good positive emotion to bring out.

6. Do you have a favourite birthday?
This is another positive emotion type question that can really open up a conversation. It will inevitably lead them to describe the birthday and why it was so good (revealing about themselves) as well as leaving lots of great opportunities for follow up questions.

7. Do you remember your first kiss?
This is a good question as I have not come across anyone who does not remember their first kiss and also introduces the thought of the act of kissing in a completely inoffensive way. The first kiss, regardless or whether it was good or bad, is normally a fun and nice memory to talk about and will open the door to related topics.

First Date

8. Do you have bendy ears?
I know, I know, this seems like a mad question, but try it and see it what happens. Some people have more bendy ears (as in they can be folded) as the cartilage in the ear is not as rigid. This is a fun thing to ask and get them to do as if you do it right, then you will get them to feel your ear and/or you feeling them. This is a fun and non-sexual way of introducing bodily contact. It also often leads to demonstrations of other odd things people can do with their bodies.

9. Who do you take after most, your mum or your dad?
This is a good lead into finding out about their family, but also will inadvertently get them to reveal the traits about themselves. If they say a bit of both (which is common) then ask them which traits they get from which.

10. Do you say either (pronounced ‘e-tha’) or either (‘i-tha’)?
This is actually a silly joke question as whatever answer they say, you will answer, ‘but which one?’ If they look confused, follow up with ‘do you say neither (‘knee-tha’) or neither (‘ny-tha’)?’ Although a silly question, how the person responds will show what sort of sense of humour they have.

Related Posts
10 Things Not To Do On A First Date
Internet First Dates
Bad Things To Say On A First Date (personal experiences)
A New Low In Ridiculous Things To Say On A First Date
Getting The Girl To Pay For Dinner

10 Great Questions to Ask on A First Date (Bounce Off)

by Jake McMillan (for the Bounce Off site)

There seem to be many sites out in the webosphere that offer advice on good questions to ask on a first date. However, I think a lot of them are quite poor as they are trying to be too clever, too relationship-focused, too confrontational or just too lame (e.g. what is your star sign?).

A good question to ask on a first date is one that helps you get to know the other person better in a relaxed manner as well as keeping conversation flowing in an interesting and fun way.

CLICK HERE to read the questions on the Bounce Off website.

10 Things NOT to do on a First Date

 by Jake McMillan

1. Arrive drunk

2. Call your ex during the date

3. Bring a gimp mask

4. Return from the bathroom and forget what she looks like

5. Do the ‘Pull my Finger’ gag

6. Talk about lack of improvements in tampon technology

7. Ask her how she feels about a threesome?

8. Suggest she used to be a Horse

9. Try to borrow money from her

10. Spontaneously combust

Related Posts:

Be Cheap in the Beginning

by Jake McMillan

I believe strongly, as a guy, that we should be cheap when starting to date someone new. I know I am in a minority when I say this.

Many women and men believe men should pay for women on the first date and that it should be men who should woo their lady with trips to nice (read: expensive) restaurants and shower them with gifts. This is all wrong and I’ll explain why.

No matter how passionate and intense the romance is at the beginning of a relationship, the reality is that this will fade and at some point or another your partner will ask you why don’t you take her out to nice places anymore or hardly ever buy her flowers, etc. It’s the same principle as when Harry tells Sally in ‘When Harry Met Sally’ why he doesn’t take his girlfriend to the airport at the beginning of the relationship:

Harry Burns: You take someone to the airport, it’s clearly the beginning of the relationship. That’s why I have never taken anyone to the airport at the beginning of a relationship.
Sally Albright: Why?
Harry Burns: Because eventually things move on and you don’t take someone to the airport and I never wanted anyone to say to me, ‘How come you never take me to the airport anymore?’

By being cheap in the beginning, it means when you do eventually make an extravagant gesture now and again it has more meaning. It’s all about managing expectations. If you spend a lot on them in the beginning, you are setting a dangerous precedent which you will ultimately fall short of, whereas if you are cheap then their expectations are low and you can only exceed them.

Therefore, being cheap is a good strategic move relationship-wise. It’s also, let’s face it, good for your bank balance.

If you’re doing a fair bit of dating and paying for all these dinners and taking women out, it can get damn expensive. You can justify the expense for the woman of your dreams, but you can’t for all the others you’re wasting your hard earned cash on.

The one down-side in the being cheap approach is that women don’t like it and may not want a second date if you appear too tight-fisted. That is why you have to start managing their expectations even before the first date begins. I always tell women I’m about to go on a date with that I am cheap and that they should expect to pay for their own food.

I hope they don’t think I am joking?

Bad things to say on a first date

by Jake McMillan

I like to think my desire to discuss fun and controversial topics is a positive attribute, but sometimes it lets me down. Namely, when chatting up women.

My love of fun banter unfortunately overrides the need to be a bit cautious when chatting to someone new. I leap in with potentially controversial topics before getting to know whether they are the type of person who can handle it or would enjoy it.

My defence in all this is that if she can’t handle such topics, which aren’t particularly outrageous, then she probably isn’t the type of woman for me. However, perhaps I could wait for date 2 or 3 before mentioning some topics and perhaps avoid some stuff all together.

Here are conversational topics which I would caution against using on a first date:

That you are a rubbish cook and have a rubbish diet

I met this girl via an internet dating site who said on her profile she really was not much of a cook. However, when I told her about my view on cooking she was quite appalled. Me saying the following things did not go down well:

“I don’t cook, I only heat when I have to”

“The fruit and veg area in the supermarket is just the annoying area you have to walk through to get to the good stuff”

“I pierce a film lid better than anyone I know”

I then spent 5mins explaining the virtues of steamed microwaveable veg.

That you sometimes put a remote control in your mouth

Why this topic came up, I cannot remember? I was on a third date and for some reason I thought it would be a good idea to confess that sometimes when engrossed in a film at home I discover I have put the DVD remote control in my mouth and am actually seeing how far I can get it in. I could usually get my mouth to the Play button but not any further without causing discomfort. I guess I was hoping she would find it funny and that she would offer some embarrassing confession too. Nope. She was silent and just looked at me in a very odd way. There was a fourth date, however.

Bringing up the scrunch or fold debate
As you may know, I love talking about this and enjoy the different arguments people have for their preferred method. Anyway, I mentioned this on a first date only yesterday and she had not heard of this discussion. She was quite a liberally-minded person, but was clearly stunned and said it was not something she had ever thought about before. In her words she was “flummoxed” by the whole conversation.

Suggesting she used to be a Horse

Click here to read the full story on this. I thought I was being funny.

Revealing that you’re an ordained Reverend

After seeing that episode on Friends where Joey gets ordained on the internet, I went online to see if it was really possible. Turns out, it is really quick and easy (check out the Universal Life Church) and within 5mins I was ordained and printed out my certificate. Some people think this is weird, however. I protest this and it has actually led to my really good friend asking me to marry her and her fiancé. I feel very honoured to do this.

Talking about Tampons
Read here for a new low in dumb things to say on a date.

The Internet Dating Myths

by Jake McMillan


It’s been around for quite a few years now and Internet Dating has become to most people a fairly acceptable way of meeting new people. Not the only way of meeting people, but just another way of meeting someone. Following some chats with both male and female friends who also partake in online dating I was surprised that they still believed some of the myths of internet dating and had not been aware of some of the cold realities of the process.

Myth:  Online dating is a place where both men and women can and will make the first move with each other

Harsh Reality: Men have to make the first move in the vast majority of cases. Women who do make the first move are ‘probably’ not that attractive.

The virtual dating world unfortunately mirrors the real world and men have to approach women and send the first message. Men who do not bother and just sit back and wait for interest in them will not, unless they are Brad Pitt, get much attention and if or when they do, it will not be from hot chicks.

Hot chicks need only to create their account and wait for the messages from eager men and pick the best ones to reply to. Average-looking women may need to ‘wink’ (or equivalent function) to get a guy’s attention and make it clear they are receptive to a message from them. Minging women need to make more of an effort online and send messages. Whereas all men, minging or otherwise, have to make the effort.

Myth:  Online dating is a quick and easy way to meet great new people

Harsh Reality: It actually takes up a lot of your time, especially if you are a bloke, as you have to play the numbers game to be successful.

You can spend ages trawling through pages of profile pictures, clicking on an individual profile to find out that the main photo was clearly taken a long time ago compared to the others. Rather than search the profile for positives, you end up searching it to see if they have things that put you off, like, for example, whether they are slim or fat, tall or short, divorced, have kids, whether they drink or not, or if they are religious and if they can write a coherent sentence? Why do so many people put up group photos when the photo is so small you cannot make out the person? Or if they do, they put up a picture where they are standing next to someone who is far more attractive? I’m always suspicious of profiles where you do not get to see their face that clearly in more than one photo.


Myth:  Women will judge men on their witty and personal opening message

Harsh Reality: Rubbish. They may not even read it. Like men, they will judge you on your profile picture and if you don’t look too bad they may even read some of your profile and if they fancy you they will reply despite what your opening message says.

I’ve heard some women complain that the opening message from a guy seems like it has been copied and pasted or is not more of an effort than ‘How’s it going?’ The majority of the time this is probably true as men know there is absolutely no point spending ages crafting a personalised and humorous message as chances are it won’t even get read. A friend of mine had automated rejection emails from girls who hadn’t even read his message!


Not so much a myth, but it surprises a lot of people how impolite Internet Dating can be as it seems to have its own social conventions and etiquette. For example, if you start chatting/messaging someone it is perfectly acceptable to stop communicating with them without explanation or a goodbye. Even if you meet up with someone, people will just stop communicating without having to go through the awkward, “sorry, I’m just not interested” conversation.

I’ve noticed that in London particularly, and this is probably true of other big cities, that people tend to play games more, which I really hate. It all seems rather false.

That being said I have met some really nice people through online dating, but think I may take a break from it for a while. Of late, I seem to have done better meeting people I like the old fashioned way!



Related Posts:
The Dating Milestones
Internet First Dates
Women Asking Men Out?
Top 5 Terrible Ways to Dump Someone 

No Sex on the First Date?!

I know I’m going to really upset both men and women by saying this, but if a woman wants to have a relationship with a guy then she should not have sex with him on the first night. I’m not religious in any way and firmly believe in the equality of the sexes, but I think there is still an inequality when it comes to sex and I am sorry to say that men are completely to blame.

Even in the 21st century, rightly or wrongly, men will still judge a woman for going all the way on a first date, even if they are the ones pushing for it to happen. I’m sure lots of men would say they disagree, but even the most liberal man will consciously or subconsciously think less of a woman for doing the humpity bumpity on the first encounter.

It does all depend on the situation and if the woman is just seeking fun then there is no harm at all, but if seeking fun but also kind of hoping this could be something special, then a man, even the good ones, will be less likely to view the woman as a long term potential if she is all too ready for a game of bury the sausage.

This is, of course, completely unfair as it seems okay for men to be proud of their sexual conquests and promiscuity whereas women are judged as being sluts for acting in the same way as it is not ‘lady’ like. I’ve even found myself occasionally judging or feeling disappointed in female friends for getting up to sexy shenanigans with guys they had just met that night, but yet if it was a male friend I would think he’s done well. I’m sure I am not the only guy to think like that.

So ‘ladies’, men are rubbish (I think you knew this already) and have double standards in this area, but don’t let us stop you having your deserved fun. However, if it’s a guy that you think might be a long term potential, then maybe wait a little bit just to be on the safe side. The character Doris from TV’s ‘Gavin & Stacey’ perhaps said it best when advising Stacey on how far to go on the first date, “A kiss, a cuddle, a cheeky finger… just don’t go selling him the whole farm”.

Jake McMillan