Drawing the line in a classmate friendship? (Update OP Page 2)

[magician5]

Screen his calls. If the number is not familiar, don't pick up. Seriously. This guy could not be waving more warning signs if he was wearing a t-shirt that said, "I am ANTI-BOUNDARY MAN!  No mere boundary can defeat me!  I DO WHAT I WANT!" 

Do not go into business with this guy.  Do not work for him.  Can you imagine how entitled he feel to your time if you are his employee?  Tell him, first-stop, no more touching you.  You're not comfortable with that. And then, tell him that his calls need to be during certain hours (10am-3pm, or similar) and they should be related to your coursework.

I would make it clear to your health care provider that even if this guy contacts their office, that he is not a friend or relative and you do not want any information about your pregnancy released to him. Also, I would consider moving your birth plan away from "his clinic."  And I would request to be a private patient when you check in for your labor.

POD 100%

I know you want to "do the right thing", but you have gone beyond that and seem to feel that you are responsible for fixing his problems, or shielding him from the harsh truth that life may make it impossible for him to follow the course he has planned. "Stringing him along" out of genuine kindness and going along with the plans you two have made would surely involve many factors that would seriously burden you, and ultimately prove unworkable. Put an end to every bit of it now, and the simpler you make the change, the better. Draw it in broad, bold strokes: "I'm afraid I won't be able to work in your business at all, my husband and I have different plans." Period. No further details.

[CrochetFanatic]

A little late for this one.  I feel bad for the guy, but he's not behaving appropriately.  Calling at too-early hours, asking about your gyno (seriously?!  ), not taking no for an answer the first time around, trying to touch your belly, and so on...that's not okay.  I'd be extremely uncomfortable, probably to the point of being immobile and compliant...at least for a while.  I'm not saying he's a bad guy, because it sounds like he means well.  At least he seems to accept a firm decision without getting angry about it.

I don't have any advice or anything, but good luck.  I've been in a similar position when a socially awkward (more so than me, lol) classmate was making me uncomfortable, and while the situation wasn't quite as drastic, I was torn between wanting to withdraw from her completely and not wanting to hurt her feelings.  I remember one time when she came over and plunked 25 pennies down on my desk to exchange for a quarter because I'd given her one the day before when she was a bit short for the vending machine, and I was so stunned that I wordlessly made the exchange before wondering what the heck I was going to do with 25 pennies...and, more importantly, how I was going to use the vending machine!  Didn't think that one through, but I couldn't really think at all at the time.

I hope things get a bit easier for you.

[Syrse]

OP here again. He called me again on my voice mail. This time he sounded very short.

'Hey, it's John. Has your family extended yet, and how are you doing? Bye.'

He keeps asking about my family, and that is just... worrying. If I send anything back now I fear he's going to latch on and demand he can come for a visit. I strongly feel he is looking for something his own son will never give him, but I am not his family, nor do I intend to become it.

Guess I'll just ignore his calls until the end of time...

[BeagleMommy]

OP, do not give this man any information.  He's hoping to become "part" of your family.  Ignore his calls if you can't change your number.  This is not rude.  If you happen to pick up the phone and he's at the other end you can say "John, I am not interested in any type of relationship with you".  Will he be upset?  Of course.  He'll either get over it, move on to the next victim or die unhappy.  I normally don't sanction this, but sometimes men of his generation take men more seriously.  You may want to have your DH say to him "Stop contacting my wife."

[SamiHami]

OP, can you block his number? Otherwise, you might want to talk to him once-and only once-and tell him plainly that your life is very busy and that you will not be able to maintain a friendship with him.

I only suggest that because I didn't see in your previous posts (although I may have just missed it) that you ever explicitly told him to back off.

[Quesselin]

To me, it seems like John has watched too many "heartwarming" movies: He has no grandchildren on his own and is worried about his mortality and the legacy he will leave behind.
He meets the OP, who is young and strong and pregnant, and thinks (subconsciously, of course): "I will become friends with that woman, and I will be her mentor, and I will be the honorary grandfather of her child! We will start up a business together, and when I am gone, I will be remembered as Wise Old John who ensured her livelihood and taught her so much, and as the best grandpa ever!"
Seriously, isn't that basically the script for the most heartwarming movie ever?

[AngelicGamer]

To me, it seems like John has watched too many "heartwarming" movies: He has no grandchildren on his own and is worried about his mortality and the legacy he will leave behind.
He meets the OP, who is young and strong and pregnant, and thinks (subconsciously, of course): "I will become friends with that woman, and I will be her mentor, and I will be the honorary grandfather of her child! We will start up a business together, and when I am gone, I will be remembered as Wise Old John who ensured her livelihood and taught her so much, and as the best grandpa ever!"
Seriously, isn't that basically the script for the most heartwarming movie ever?

... Didn't I just see that movie on the Hallmark channel? 

OP, I'd go with the advice given here.  John sounds...odd.  There are other words, but I think I'm going to stick with odd.