Answering Some Questions on Online Dating

A friend, who writes the blog “Being Female…” recently wrote about her experiences on dating in her 30’s, with a focus on online dating. As part of her write-up, she wanted a male point of view as a counter-balance, so she sent me a dozen questions to answer. I didn’t manage to get my answers written up in time for her publishing the original article, but a promise is a promise, so presented below are the answers I sent through to her, plus a couple of anecdotes, which should be appearing as another blog post on her site in the near future.

These are just the straight answers to her questions. I’ve started writing up a wider PoV post, but it’s taking a while, so keep an eye out for it in the future.

Online Dating. Not for the faint of heart.
Online Dating. Not for the faint of heart.

1. Why did you decide to go with on-line dating as opposed to ‘regular’ dating?

To give me more opportunities to meet someone. By the time I was single and dating again, my social circle had shrunk and were nearly all settled down. Plus you can’t go bar-hopping all the time! Online dating opens up your options by giving you more chance to meet people you might not otherwise.

2. How did you go about choosing your preferred site? Did you do a bit of research, and did cost play a factor?

I’d heard of most of the “major” sites before I started out, so I took a look at those. Over time, I’ve tried out most of them. Trying them out for a few weeks is probably the best “research” you can do. Each site has subtly different cultures and etiquette, so you almost have to “date” the dating sites at first to find the one you’re most comfortable with.

I’ve come to the conclusion that paying for a dating site isn’t really worth it as there’s so much “crossover” of people between the different sites. Plus paying for access to the site puts extra pressure on people to “get their money’s worth” (probably tying into the answers to 3 & 5) There’s an argument to be made that price filters out some of the really bad people (see – creepy/abusive messages) but equally, paying for something gives some people a sense of entitlement, making them just as bad.

3. Were you nervous when you first created your profile?

Not really. It depends on your attitude to things, I guess. If you’re keen to meet “The One” as quickly as possible, then you’ll put yourself under pressure to get your profile right, which is where the nerves come in for some people. I treat it like filling in any social media profile.

Relax, take your time, and learn to evolve your profile over time. Keep track of what changes you’ve made, and refine what’s in your profile based on what works.

4. How quickly was contact established – did you have to wait a while or were there instant messages?

It depends. If you’re the “new guy” then you can get pounced on pretty quickly on some sites, depending how much “choice” there was before you started showing up in search results. It also depends how good your profile and pictures are. I’ve had experiences where I’ve had a message within 30 minutes, and others where I’ve not had any in the first 2 weeks.

In my latest “go” at Online Dating, I created my profile one night while I was in San Francisco for a few days, thinking I was setting things up for when I got home. I woke up to dozens of “X likes you” alerts and several messages. I pretty much face-palmed myself as I was catching my flight later that day and so couldn’t follow up on any of them. Ladies of San Francisco: sorry!

5. One of the ‘myths’ about on-line dating is that the sites are populated by people who are desperate and a bit ‘strange’ – did you chat to anyone who you felt fit this description? Any funny anecdotes? (no names needed)

A couple have fallen in the “strange” category, but they’ve been the minority. It also depends on your definition of strange – I’m sure I’ve probably come across as “strange” to some people! It’s all relative! Sometimes the “strange” ones are the more interesting and fun people you meet.

As for “desperate” – btw, I’m not a fan of that description – I’ve talked to people who could match that stereotype. There’s been a few who place quite a lot of pressure on themselves to “meet someone” and often don’t realise it… and as a result they can come across quite “full on” and be very demanding. I try to give someone the benefit of the doubt though; you don’t know them well enough to know if there’s some external factor causing them to be stressed out.

6. How quickly did you meet any of the people you chatted to?

It depends how the messaging goes, “schedules,” and how open someone is to meeting a stranger off the internet1. Some people I’ve kept talking to online but never met.

For the people I have met: shortest time – a few hours. Longest – 5 months. On average, it is usually around 2-3 weeks.

7. Did the person/people you have met live up to their ‘chat’ i.e were they telling huge whoppers on-line to reel you in, only for you to discover they were nothing like that in real life.

The biggest disparity is usually in how they look in their pictures vs. how they look in real life. I’ve met people in person who barely resemble the person in their profile pictures. Side note:- having nothing but group shots with your friends in your profile is a massive pain2.

“Chat”-wise, often I’ll find someone isn’t quite the same as their online persona, but normally not deal breakingly so… they’ll be quieter, or less out-going, or not quite as into something as they maybe gave the impression they were. Alternatively, they might go all-out to impress, and end up not presenting themselves in the best light. I often put it down to nerves and try not to judge too much on just that initial face-to-face.

Tying into answer 9, some have turned out to be far more shallow than they seemed in their messages, which is always a disappointment.

8. Have you had a relationship with someone you met online (For purposes of the blog, I would probably define a ‘relationship’ as being with someone you have dated exclusively for 4 months or more, but I know these things are dependent on situation and do not follow any prescribed timescale – people develop feelings or fall in love at their own pace)

In those terms (and probably in any other sensible definition) – no. Most have been 2-4 dates, then realise it’s not what one (or both) of us are looking for and fall out of contact. Some have been a few dates, then it develops into a friendship rather than relationship. Others have just been random, almost haphazard… date one or more times, fall out of contact for a while, get back in contact, repeat.

9 Do you think people on-line don’t give dating relationships a chance to work i.e. rather than work at getting to know a person, if the person doesn’t meet the picture in their head from the get go, they move onto the next person quickly. The grass is always greener syndrome – looking for a partner where no work is involved in the longterm.

Absolutely. I’ve had some horrific experiences with this that have nearly put me off the online dating thing entirely. Obviously you need to “click” with someone, and find them (at least moderately) attractive, but there’s been times where I’ve met someone after exchanging messages + photos for a few weeks… and you could see the disappointment written all over their face when we actually met. Which makes you wonder how much attention they were paying in the first place, but never mind. Not surprisingly, those dates didn’t last very long!

By all means, you can know by the end of the first date if someone is or isn’t a match, and some things are decent indicators… but I’d question if you can accurately tell within the first few minutes like some people I’ve met have done. At least give it until the end of the date and any follow-up communication3.

10. How many people do you think it is acceptable to date at any given time?

I wouldn’t say there are any hard-and-fast rules here… it would depend how much effort you were putting into establishing relationships with the people you are dating. If you’re actually trying to build a solid relationship, I don’t see how you could honestly date more than 1-2 people at a time. Maybe 3 at most, if you have the time. But equally, if you’re just starting out, there’s no harm in having a different “first date” each night of the week if you’re able. As time goes by, you’ll naturally find yourself dating less people at once as something becomes more serious.

If you are planning on “dating around” with multiple people, it’s only fair to be upfront about it so there are no misunderstandings!

11. How long would you date someone before removing your profile from a dating site, if ever?

No set rule… whenever you feel “comfortable” in the relationship, I guess. With my last girlfriend (who wasn’t met online) I took it down after about 4-6 weeks, partly because she was away for 2-3 weeks of that time and it wasn’t certain things were taking off.

12. Any other comments or observations you would like to make?

I could probably write a book here, but I’ll keep it to only one aspect:

Online dating can be both a very rewarding experience of meeting interesting new people, some of which you’ll share some good (possibly great) times with… and the most exhausting, dehumanising, soul-crushing experience I’ve come across. One minute you can have your ego inflated and be feeling pretty good about yourself; then you’ll find it burst, torn to shreds, set on fire, then the ashes blasted into the cosmos.

Over the 2-3 years I’ve been using online dating, I’ve rarely been able to keep at it for more than 3-4 months before I need to take a break… by which I mean completely take down all profiles (delete, not just disable), unsubscribe from any email newsletters, and remove any apps from my phone. I’m in the middle of such a break just now.

“Burnout” is a very real thing you have to be careful of. You also should be in the right frame of mind before starting online dating, or you won’t give the best impression of yourself – leading to less “success” when going on, or even in attracting dates – creating a downward spiral.

Never, ever, ever jump straight into online dating on the rebound. Ever. Trust me on this.

So why do online dating at all? Because when you do meet someone you click with (even if it’s only for a short time) the feeling is awesome. When online dating works, you’ll have a lot of fun, and meet some great people along the way. One of whom might be “The One” you’re looking for – which is the whole point really.


  1. Yes, really. Some people do go into Online Dating reluctant to meet anyone they’ve met on the Internet. 
  2. Don’t be that guy/girl. Please. For your own sake. 
  3. Speaking of – if you do a vanishing act (ignoring messages, etc) after spending a couple of weeks getting to know, and then going out on a date with someone – then you suck. It doesn’t cost anything to at least say “hey, sorry, things didn’t ‘click’ for me.” You might not be interested, but there’s no need to be an ass. 
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