Should I keep messaging?

[Jumpinginwithbothfeet]

Been speaking to a seemingly nice guy on OLD for 5 weeks! Have suggested meeting up a few times he always says yes but never gets round to agreeing a date. I do not want to keep asking. He has a fab sense of humour and I have checked out his social media and he seems to be exactly who he says he is. We both have kids and work so can be tricky to find spare time but surely if he was as interested as he implies he would have found some time by now?! He does come across as a little shy but is it worth carrying on with the messages?

Personally I wouldn’t be happy with this, no. My boyfriend who I met through OLD asked me out on the first day and about 5 messages after we matched. I would have asked him out very shortly if he hadn’t! We are busy people (him with his work, me with dd) so it wasn’t easy to arrange the first few dates - indeed he cancelled our first booked one as he had to work late. But it was evident the intention was there…..

If a man (or woman) is keen on actually dating you, I reckon they will show that.

Lots of people do OLD looking for a pen-pal, as far as I can tell. Nothing wrong with that at all if that’s what you both want. But if you want to meet up in RL, sounds like this isn’t the guy for you……

[quote Jumpinginwithbothfeet]@Peach01 minimal flirting, more general chit chat. Although he seems quite shy...for example I asked for his number as had been chatting via app and he happily gave it and said he had been wanting to ask for mine but wimped out. So not sure if that's why or there's another reason[/quote]
Ah okay. It's either that he might not be good with this type of thing, or he's not all that interested. If it's the latter then forget about him, if it's the former then you do really want to have to graft?
I always think a way to tell if someone likes you is how much effort they put in for you. Given you've already asked to meet up and he's avoided committing to it, I'd hold back. I personally wouldn't initiate contact but I can understand why you might want to. With him being too shy to ask for your number from the start, you'll always wonder if he's needing a push. That sets the dynamic for you feeling you need to take the lead or be left in limbo not knowing if it's his shy personality or if he doesn't want to.
At some point he needs to instigate it if he wants anything more.