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What are some questions I should ask him on tomorrow's first date b/c I am nervous about him being a divorced single dad?

37 replies

ForeverHopeful3 · 26/07/2025 05:23

I am going out on a first date with a man who I have been chatting with for the past two weeks. We've talked on the phone a couple of times and have pretty good chemistry so far. I am excited to see him tomorrow night! He is driving almost 4 hours to come see me!! (We will live that far apart... don't know how we matched lol)

I am 33, no kids/never married and he is 41. He told in our first conversation that he was a single dad, divorced for like ten years. I was pretty surprised but I liked his energy a lot so I didn't let that stop me from seeing where this goes.

But now I am nervous because I was not planning on being a potential step mom. And I was not thinking about getting into a relationship with a divorcee... My parents are going to have a fit lol

I am scared that his daughter won't like me (she's 11) and his ex-wife is going to cause all sorts of issues.

OP posts:
Splendiddydody · 26/07/2025 15:55

The first step is to see whether you actually like each other in person. Having said that, you seem to have way too many reservations so I’m wondering why you are actually bothering with meeting him.

Crushed23 · 26/07/2025 16:01

Honestly? Forget it. You’re only 33, the dating pool is plenty deep to find a man who:
-lives closer to you
-is in your age group
-doesn’t have more baggage than Heathrow

Good luck.

Mom2K · 26/07/2025 17:24

4 hours away? I'd be wondering if he isn't actually divorced.

I think most people wouldn't want to start something with someone that would be difficult to see frequently due to distance. Especially a 'single' parent, because getting the time when you have kids is already a challenge.

The dude is probably still married and doesn't want to get caught. I mean, maybe not...but it's weird.

Ohitshot · 26/07/2025 17:31

What happens if you don’t like him on sight? Happened to me several times. Once I drove to meet someone (not far fortunately) and I passed him as I was trying to park. My heart sank as I knew even from a distance without talking to him that he was not my ‘type.’ I did meet him but I wasn’t interested.

What a waste of time it will be for you if you build it up too much! Can’t you find someone who lives in your town? I have a friend who met someone online and after a few months of chatting she went to stay with him and he lived a few hundred miles away. It got really awkward as she wanted to leave and found it hard to tell him. She wasn’t in danger but she didn’t want to hurt his feelings.

Geesgirl · 26/07/2025 22:04

Based on the comment about your parents, don't waste his time.

SecretNameforMN · 26/07/2025 22:56

Don't do it! You live too far apart

GreenOtter · 27/07/2025 07:38

I would be worried OP, this guy does not sound like good news. You say he is divorced about ten years and he has an 11 year old. So he divorced his ex when the daughter was one or a small toddler? This is a huge red flag. The first year of having a child is very hard and the support of a partner is paramount. My first question would be why did he want out of the relationship?

For me, knowing he left when the kid was so small, would be enough to not see this guy.

He could also be lying about something. Driving four hours is intense. Seems like something is way off about him.

EnglishRain · 27/07/2025 08:33

The distance is the big issue. I wouldn’t date anyone more than maybe an hour and a half away. And if they were super stuck geography longer term it would need to be closer. DP and I were 45 mins away and he nearly said let’s not bother before our second date as he was worried about the distance.

Lushvegetation · 27/07/2025 09:09

Someone who is married or in a relationship looking for sex would do that drive but not someone who is seriously looking for a relationship and thinking about their child. You’re being very naive.

Bananalanacake · 27/07/2025 09:28

You need to wait in a relationship to meet their kids, I'd give it a year and a half.

MrsSunshine2b · 27/07/2025 12:19

Do you want your own kids?

The stepmum path is not for the faint of heart.

I completely disagree with not discussing this stuff at the outset. If he's a decent Dad, his daughter will be coming up in conversation anyway and if she doesn't that's a bit of a red flag in itself.

I'd be looking out for:

  • Badmouthing the ex, seeming angry, bitter and resentful
  • Limited or no contact with the child
  • Making excuses for why he can't be a present, decent dad
  • Seeming overly enmeshed with the ex, still doing "family" activities as if they haven't actually broken up
  • Being a Disney Dad and showering child with gifts

This is also a good time to talk about your philosophies and opinions on parenting because this is going to make a big difference to whether the relationship has any potential.

You don't want to get too deep into this before you see the red flags. A dysfunctional family is miserable, a dysfunctional blended family is hell.

Bittenonce · 27/07/2025 13:42

4 hours? That’s serious long distance!
Which means any time you meet, you’re going to spend the night together….
And it’s never easy to get to know each other properly. And you can’t do anything spontaneously.
So if all you want is a fuckfest every other weekend when he’s not with his kids, I guess is fine. It’s probably what he wants!
Just depends what you want….

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