Wasn't sure whether to post here or in relationships or lone parents, and not really sure what I'm after. Basically some general encouragement and advice, I think!
Have been dipping my toe into the murky waters of online dating and exchanged several messages with a guy who seems well-educated, fit and interesting. He wants to meet up for a drink. (Yay!) I would really like to as I am keen not to fall into the endless-messaging-no-meeting trap. However...
I haven't been on a date since I met my ex husband 10 years ago. The circumstances of our split involved quite a hefty blow to my confidence and perception of my body, and I never had the greatest self-esteem anyway.
I'm 28, 5'8, a size 12-14 with small boobs, slight muffin top and a spotty chin. By spotty I mean big pre-menstrual cyst-type spots which are now reducing in size, thankfully, but might still be slightly noticeable on the day he has suggested. I have absolutely no money this week, so buying something new is out. I rarely wear heels. The only smart shoes I have are brown brogues and black suede Wallabee wedges. (Love them, but they might be too 'grandma' for a first date?) What should I wear?!
He's into clubbing and I've not done that for about 6 years. I don't do a whole lot besides work and childcare. He's got loads of friends according to Facebook stalking, most of mine disappeared as a result of the split.
Also, I will probably be on my period. I'm not intending to shag him anytime soon anyway, but is this a bad idea for a first date?
I'm also a single mum and haven't told him (didn't put this in profile to be on the safe side). When is the best time to tell him? He seems generally positive about children, and I wouldn't introduce anyone to my DC for several months anyway. I'm also theoretically married and only just starting the divorce paperwork... If the situation were reversed I know my red flag alert would be deafening!
I blush easily and when I'm nervous I don't talk a lot, and when I do my voice gets very squeaky. I'm rubbish at small talk.
Basically, this is going to be a disaster and I just know I will go home feeling rubbish about myself, but as I'm having another Saturday night on the sofa, I'm thinking I should just go for it. I've been single for 3 years, so it's about time. Please help 
in advance!