Dating in Your Thirties – Those Awkward, but Important, Questions

Dating Advice and Relationship Commentary


The Rugby Boy and I hit the 6 month mark last month.  To be honest, in the past, that’s been something of an ejector-seat button for me and relationships.  It’s been a running joke throughout the early stages of our relationship that The Rugby Boy will be entered into the Guinness Book of Records for reaching that particular mile-marker.  It’s a slight exaggeration, and I’ve probably spent 6 months in a relationship with half a dozen guys over the years.  They just didn’t make it much further.  But it’s interesting, because all of those relationships were in my teens and twenties.  And suddenly being in my thirties adds a different spin to the relationship.

The Six Month Mark

The thing about being with someone for 6 months, is that it feels like a relatively long time.  We have an extremely ‘adult’ relationship.  We spend 4 or 5 nights a week together, out of convenience, as well as comfort, and in the last 6 months, The Rugby Boy has become my best friend.  He knows my odd little quirks, and can read my moods, and we’re completely comfortable around one another.  And yet it really is ‘just 6 months’.


Why Six Months Is No Longer Trivial

At the weekend, I went to Go Ape with a group of The Rugby Boy’s best friends, and one of them introduced me to her brother-in-law.  ‘This is TRB’s new girlfriend’, she said, without a thought.  Because to her, I am his new girlfriend.  It’s only the third time I’ve met her, and for all I know, the last time TRB saw her brother-in-law, maybe he had a different girlfriend.  And yet the comment stung a bit … because after 6 months together, things don’t feel all that new at all.

The Older You Get, The Quicker Stuff Moves

I’ve commented before about some of my original 30 Dates, and just how much their lives have changed in the 18 months since the challenge ended.  One is married, another is engaged.  One guy who asked me out during the challenge  (but who I turned down, because I knew him already) even has a child now!  A LOT can change in a short space of time.  And so, whilst 6 months may seem rather ‘new’ when you’ve been with your husband over 10 years, when you’ve been single (and picky!) in your thirties, getting to the 6 month marker with someone is a rather big deal.


Dating In Your Thirties

If you’re female, want children, and are in your thirties, you’re unlikely to engage in petty flings any more.  Frankly you don’t have time.  No, this isn’t a panic about biological clocks, but there is a certain reality that if you’re looking for a longterm relationship, and are hoping to be married within a couple of years, you’re not going to waste your time on relationships that aren’t going anywhere.  You’d rather be single than wasting your time.  Which means, if you do make it past a couple of months with someone, it’s because you’re at least toying with the idea of a future with them.

Which Leads to the Awkward Questions

When I first went on a date with The Rugby Boy, he complained that all the women he’d met on would practically interview him on arrival.  He’d be on a first date, answering questions on marriage and children … awkward questions which you should never bring up on a first date.  BUT … questions which a few months in, are actually quite important.

Yes, the world outside may see you as a ‘new’ relationship, but in those initial months, you need to decide if this is someone you want to ‘waste’ your time with.  Is there a possibility of a future?  Is it worth a gamble, to see where things might lead?


Wait to Ask the Questions

The key is timing.  Yes, you need to know if he has the same future goals as you.  Yes, you need to know what he thinks of marriage, and children, and how he sees the next ten years panning out.  BUUUT you don’t need to know these things on a first date.  Let yourself work out if you like him first!  In all honesty, if someone is particularly adverse to marriage or having children, and is of the age where it is normally a consideration, they will normally tell you pretty quickly.  And you can normally begin to gauge someone’s stance on children just from the way they interact with other peoples’ kids.  Spend some time working out if the rest of the stuff lines up before you start having those awkward conversations.

But don’t put them off too long

Personally, I don’t plan to have children for at least another couple of years, but when the topic came up at dinner the other night, it didn’t scare me.  As far as I’m concerned, there’s an unspoken rule when you commit with someone in your thirties, that you both see each other as at least marriage potential!  If not, why are you together?  I mentioned our conversation about kids, in passing to a colleague  (purely because of the funny way it was brought up …. both the Rugby Boy and I put our hands under the table and held up how many kids we hoped to have in the future!) and she was shocked.  ‘Cor, that’s a bit quick isn’t it?’  Well no … actually it’s not.


I’ve spent 6 months dating The Rugby Boy.  I know what he’s like.  I know I enjoy his company, and I know I care about him.  It’s been 6 months of my thirties … and whilst I don’t want to leap down an aisle any time soon (or onto a labour ward!) it’s not unreasonable to check in and see that his ideals for the future are similar than mine.  Because 6 months may not be a long time, but if I were to spend another 6 months, or a couple more years, finding out the answers to those awkward, but important, questions, I might find myself regretting ‘wasting’ my thirties on someone who doesn’t have the same ideas for the future as I do.

Miss Twenty-Nine xxx

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