On May 16th 2001 iVillage hosted its first live chat with Dating Doyenne, Sally Ann Lasson. If you missed it, here’s what happened.

detak24: Do you believe in The Rules?
Sally Ann Lasson: I’m afraid that I do. The book’s a bit daft, but it’s a handy reminder of some of the basics of dating. You know, not calling, etc. But I think you can have sex.

kensey_16uk: I like this boy called David, but I don’t want too ask him out because we are close friends. What do you think I should do?
Sally Ann Lasson: Hi kensey, I’m never sure how you go from being friends with a guy to being romantic. Why didn’t you two get it together sooner? At any rate, handle with tact in case your feelings are not reciprocated.

violet_willis: My boyfriend is incredibly stingy! How can I get him to get his wallet out?
Sally Ann Lasson: Hi violet. A stingy man is a bad man and, of all the character flaws there are, this is the one that’s incurable. He’ll never get his wallet out because that would involve sharing.

esmeralda20001uk: How do you know if a man is really serious
Sally Ann Lasson: Dear esmeralda, this is one of those things that you have to rely on your instincts to determine.

chilligerkin: What is the best way to get out of a boring date early?
Sally Ann Lasson: Hi chilli. Say that your cat is at the vet’s and you have to collect it. Cry. Or best of all, tell him you love him and want to have his babies. You’ll be home in half an hour.

dixiechick1_uk: Why am I attracted to men I can’t have?
Sally Ann Lasson: Hi dixie. Maybe they’re the good looking ones that we all want. You have to compete – no guts no glory.

teabreak747: What’s the best way to ask a man out on a date? We work together and I don’t want to die of shame!
Sally Ann Lasson: Hi teabreak. Ask so casually that he’s not sure whether you’re asking him out as a colleague or a prospect.

slim_frog: How do you get a relationship going again after you’ve broken up 3 times?
Sally Ann Lasson: Hi slim frog. Well, I suppose that if you keep getting back together you must be very attached to one another. What you need to do is work out the causes of your separations and how you can build a few bridges. Break-ups are painful – it would be better to avoid such dramas with more conversation and problem solving.

skankpantyface: How do you know if your girlfriend is ready to accept a proposal of marriage?
Sally Ann Lasson:Hi skank. Well, there’s supposed to be a little anxiety on the man’s side. It’s all part of the excitement, but the fact that you’re considering it must mean that you have a hunch the time is nigh. Give it a go. Good luck.

curlysue2: Not strictly dating, but what the hell! How do you know when it’s the right time to move in together?
Sally Ann Lasson: Dear curlysue, I hope it’s something you would both know.

chilligerkin: Do you think a 10 year age gap is too much?
Sally Ann Lasson: Hi chilli. Ten years is the maximum age gap permissible. but fine.

stuckforlove: How do you approach your best friends sister?
Sally Ann Lasson: Hi stuckforlove. It depends on your best friend, I suppose. Would they be cool with it? Ask her out in a roundabout way – but I’d check with the sibling first.

dolly_princess3: My boyfriend says he hates me and never wants to see me again, should I persevere?
Sally Ann Lasson:Dear dolly, no. It’s always a good idea to listen to what people say and to respect it. Pride is a cold bed mate, but better than nothing.

libbyandrew_99: I am really good friends with this guy, but we act like we hate each other (in a jokey way) and I have been told by everyone that he likes me.
Sally Ann Lasson: Hi libby, this is called sexual tension. It needs to be turned to constructive use. Try approaching him in a softer way – he’ll probably respond in kind. You obviously like each other.

angharad_t: I fancy my mate (who’s a boy) and don’t know how to tell him. Help!
Sally Ann Lasson: Hi angharad. Don’t tell him you fancy him because it might frighten him too much. Try showing him and see if you get any signals back that let you know how to proceed.

papa_roach_ukmtc:Is sex on the first night wise or not?
Sally Ann Lasson:Dear papa roach. Its neither wise nor unwise. Practice safe sex and have it whenever you fancy it. First dates are a good time to establish a sexual relationship. If you put it off it can all get a bit awkward later.

karat26: What’s the nicest way to dump someone? And do I have to do it in person?
Sally Ann Lasson: Dear karat26. Yes you do, because that is the honourable thing to do. It involves a round-up of the usual sentences like: I’m not ready yet / I need time / It’s not you it’s me.

t00the: I think this girl likes me but I am too scared to ask her out
Sally Ann Lasson:Hi toothe. Dating is fraught with anxiety and it starts with the first date. So hold your metaphorical nose and give it a go. What’s the worst that can happen? She can say no and then you’ll only be where you are now.

hellboy1313: Is it true that if you have sex on your first date, the relationship won’t last?
Sally Ann Lasson: Hi hellboy. Where do you get these ideas? Why should it make any difference which date it is? Your heart won’t care.

disco_dolly: My boyfriend invited me out for a dinner meal with his parents and I got very drunk, embarrassed myself and now he will not speak to me. What shall I do?
Sally Ann Lasson: Dear dolly, oh dear oh dear. I’m sure he’ll come round but you might have to prostrate yourselves with remorse first. I expect you were nervous – that’s not a crime.

sloanio_99: I’ve been going out with my boyfriend for 2 years now and we work all day and are too tired at night to ‘get close’. I’m afraid he’s going off me. What do you suggest?
Sally Ann Lasson: Hi sloanio. This is the sort of thing that knackers a relationship because your bloke needs to feel that there’s some substance and empathy between you to continue. Make time – you already know that it’s a problem and in that understanding lies the solution.

lilhornydeviless01: I have a male friend who gets really jealous when I talk to other lads. Does this mean he might want more than friendship?
Sally Ann Lasson: Dear lilhornydevil. It could do or he could just be a bitter person who can’t stand the sight of someone else having fun.

cheeky98uk: Would you always recommend chat up lines?
Sally Ann Lasson: Hi cheeky. Yes. Try I’m very rich and a bit of a stud. If that fails, ask them what their favourite films are. People can go on about this for ages and before you know it you’re married.

bristolsk8er: I’ve just split up from a long term relationship after my girlfriend cheated on me, and now I’m a bit scared about having another relationship.
Sally Ann Lasson: Hi bristolsk8er, give yourself a break. You need some time to regroup your emotions until you feel like going into battle again. Take it slowly and eventually you’ll meet someone worthy of you. Good dating.

More on Sally Ann Lasson.
Read what she has to say about:
Lecherous men
Dumping someone, nicely
Finding Mr Right