When is it "too late"?

Greetings all! This is a very helpful site and I’m hoping for some clarity. My son, who rows, is taking OV to Cornell and Yale in September. He’s still waiting to hear from Princeton and Penn, both of which have expressed interest and have kept him “on the hook” with hand written notes and phone calls. I’ve told him his chances of getting OV from these two schools seems slim now that it’s almost the end of August. Am I wrong?
Don’t want to burst his bubble but want him to move on and focus on the schools that have invited him…

My daughter is in a slightly different situation, as she is a D3 recruit, but by mid-August she had visits offered from two of her top three schools. The third school had done a positive pre-read and we knew that the coach would like her for the team but that she wasn’t one of their absolute top recruits. I counseled her to send an email to the coach letting him know how much she liked the school and the program, and that she was hoping to return on a visit this fall. We figured that she had to know where she stood to be able to figure out her chances at this school. He quickly returned her email and offered her a visit.

If I were your son I would just ask the coaches at Princeton and Penn whether they could offer him the opportunity for an OV this fall, instead of sitting around and waiting and wondering. As I counseled my daughter, the worst that can happen is they politely say no, they have no more spots. But at least you are not left wondering.
Btw, this was very hard for my daughter to do, as she is somewhat introverted and these things do not come naturally to her. But when I explained to her that she really had nothing to lose by reaching out, expressing her interest and asking, she agreed.
Hopefully if this is bad advice for an Ivy OV query someone else with specific experience will jump in.
(She is a swimmer and not a rower)

Thanks so much! Your advice gels with what I suggested to my son but he seems to think it would be pushing it. I’m of your mindset that the worst that can happen is they say they have filled their spots. At least then he can move on.
I think he’s also thinking he may be in that second tier recruiting set and that if he waits he will hear something. It’s difficult to keep a positive outlook on that front. I just wish these coaches would be upfront.

Think of it this way: if your son is in that second tier recruiting set for a college, and the coach gets to the point where he is going to reach out to second tier recruits, whom is he going to contact first? Likely the recruit who he knows is still interested in coming on an OV and has continued to express their interest in the program, right? Just more argument in the “can’t hurt to ask” category. I guess I just can’t see a coach being put off by someone asking to the point where they wouldn’t consider him down the line if not for the inquiry regarding an OV. If done politely, I just don’t see the harm. I think many of these coaches will be up front if asked directly. And do you really want to deal with one who isn’t?

Good point! At least it shows determination and commitment and you’d think coaches would appreciate this.
In any case it will be nice to have it settled either way.
And my son, like your daughter, doesn’t enjoy putting himself out like this but it’s a good practice in self advocacy.
Thanks again

The recruiting season begins in September, and HYP generally have their recruits in place early, but the other Ivies are likely to be offering more OVs after the September dust settles and the first-round recruits have made their choices. My oldest said he had friends still getting offers in late fall.