Workplace Awkwardness

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I should have stated that my biological clock is ticking, and then asked how he feels about paying child support.

C’est la vie!

It’s very hard to think of appropriate things to say when one is engaged in an uncomfortable conversation.

It sounds like he doesn't respect boundaries like marital and professional.

Tell him you're like Hugh Grant from About A Boy. That makes them run.

I agree with KimD (although personally I think the guy may not have mean't any harm) that he has put you in an awkward position. If he has asked you out AND flirted with you and it made you uncomfortable then you are entitled to go to your joint supervisor and disclose this happened.

Keep in mind the moment you go down that road the working relationship with your colleague is likely to be destroyed so you need to be very sure this is effecting your ability to work as a learning assistant. You need to play this by ear and gauge your response based on the guy. If he's a nice person (it sounds like you do like him) then let him down gently. If he takes it well and acts professionally then please just move on. On the other hand if he subsequently makes you uncomfortable even after dropping hints then definitely pursue this with the school HR/Management.

I’m not an assistant. I’m a special education teacher. I’ve provided learning support services to a student in his classroom.

This isn’t so much about how to handle the situation. It’s more about handling the awkwardness of it.

Oh I see (beg your pardon). Well this is now awkward

But on a serious note, it really depends on the dynamics of both you and this gentleman. Without knowing your personality (or his) the generic approach here is to take all this in good humour. I think women should in general learn to take a man's interest in them as compliment (rather than an insult). It means you are still attractive to other men. And then that's where the humour comes into it. But it also depends on him. If he makes you comfortable (when he isn't hitting on you) then just take this in your stride roll your eyes in a joking manner and change the subject.