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How do I start regularly dating a man I've only sporadically dated before?

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Question - (9 July 2013) 1 Answers - (Newest, 11 July 2013)
A female New Zealand age 36-40, anonymous writes:

I'm 28 and he's 38. We'd been in touch sporadically over the past five years and went on a date yesterday. It's not our first date ever, but before this we've mostly either been on coffee dates or hung out with other people, so dinner and a movie felt like an upgrade. And I think I want a next date rather soon.

As I recall, he had always made the first move, either in getting in touch with me or making the date happen. The last date we went before this was probably about 6 months ago.

Before that I was in a relationship with someone else, and though we also sporadically said hello online, he respectfully backed off whenever I responded to his invitations with a "Sure, let me discuss the time with (my then boyfriend, who has met him), I'm sure he'd be looking forward to catch up with you."

On the other hand, I don't really know his romantic history because it's never come up and there aren't any hints in his Facebook page either. I'd like to think he's single every time he got in touch, but it's hard to imagine anyone that attractive staying single the whole 5 years I've known him. The point is, I'm not sure where he's coming from and what he's looking for, and though he's currently a friend, he's definitely not friend-zoned.

I'm not sure how much I like him yet (or vice versa), but he's good company, attractive, well-mannered, we share similar values and have some common interests, and I think he probably can be good relationship material. I guess the only way to find out is to score a next date soon.

What should I do? Most people say that women shouldn't do the follow up in order to score a "second date", but as I said, yesterday wasn't our first date, and I have never followed up before. Neither has he, really, but then we've been on half a dozen dates before and he's always made the first move.

And if this makes any difference, next weekend happens to be my birthday and I don't really have plans yet (because the friends I normally spend it with are only available the weekend after for a belated hangout). If it weren't my birthday, I'd consider inviting him out for dinner followed by a music gig and hope to learn more about him and his goals in the conversation. But since it's going to be my birthday, would it be awkward to spend it on a date with someone I don't normally invite to my birthday?

And it just so happens that the next weekend is his birthday as well. Likewise, I've never celebrated any of his birthdays either.

What's the best way to get a next date with him?

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A female reader, Dorothy Dix Australia +, writes (11 July 2013):

Hi there. The one thing is you don't want to come on too strong, and seem desperate.

Even though it is more than one date you have been on together.

And as he has always made the first move - in asking you out - it is probably wise to still let it be this way.

If you were to ask him out, he might think you are being pushy or controlling.

And so you don't want that.

PLUS, you don't want to scare him off either.

Why not just see what happens, and if he asks you out or not, and go from there?

You don't want to FORCE things to happen, that were otherwise not going to happen that way, as it could spoil what you have now.

You don't want to lose him altogether - even as a friend.

There is a delicate balance here, so you need to be very careful before you make any unwise moves.

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