When you’re a mama to an only, particularly one with a diagnosis for which social deficits go hand-in-hand, it’s easy to become a bit obsessed with scheduling time for him to hang with friends. Martin Luther King Jr. Day–that one January school holiday and a day when my office is closed–has been a great day for a play date.

But the stakes are high, since there are no “how about tomorrow’s” built in.

Over the years, I’ve learned some lessons about how NOT to be successful in providing my kid–who is well liked–with a friendship experience on those treasured “we’re both off” days. Following are five play date scheduling missteps to look out for:

1. Approaching Mom-of-a-classmate you’ve just friended on Facebook. While you may be eager to get something on the books for your child and a classmate he speaks fondly of–maybe even whom a teacher has mentioned has a nice budding friendship with your kid–it’s too risky. Perhaps she doesn’t use Messenger and you’ll never get a reply, or you don’t yet know she’s not one to keep a commitment. Most likely, she’s got her own close buds to make plans with anyhow. By all means, pursue a play date. Just avoid a day when you really, really, REALLY want your kid to have plans.

2. Targeting an acquaintance who happens to be a stay-at-home mom with a houseful of kiddos. Friends with big families can make great play dates. In my experience, their moms may be more than happy to schedule a drop-off to have the opportunity to get errands done with one less in tow, and their children say nice things like “I love how quiet it is here!” about your house. But I’ve been burned one too many times by a harried mom who remembers at the very last minute that, for example, she scheduled back-to-back dentist appointments for the entire clan because it was their day off from school. Her kids have built-in playmates at home, so she’s not likely to view a last-minute “oops, sorry!” as too big of a deal. Unlike me, parent of an only.

3. Calling on an old friend known to blow you off. You go way back and your kids are the same age, so it’s only natural you’d want to carry that friendship on to the next generation. Problem is, this friend, while quick to suggest making plans, gets indecisive about solidifying them. And when pushed, she may agree to save the date. Only some vague something always tends to come up on the Big Day. In other words, it’s a big no-no to reach out to this (but-she’s-like-a-sister!) friend about a single day off.

4. Waiting too long to schedule. While you don’t want to be trying to pin someone down a month or more in advance (especially with a January holiday), waiting until a few days before the date doesn’t leave much leeway for missed messages, non-prompt replies, or alternative option-strategizing. I’ve found a week or two prior is ideal. And if one family is unavailable, there’s time to ask another friend.

5. Being vague about options. With a close friend, deciding on a date and leaving the “what and where” open may work. And it’s best not to approach newer friends with one take-it-or-leave-it idea only. I’ve had luck with throwing a few options out there: “How about indoor mini golf or meeting up at the Peabody Museum? Or there’s that new Disney movie coming out. Maybe we could catch a matinee and then grab lunch.”

Another approach that has worked well for us: Texting or Facebooking a bunch of parents at once with a group outing idea, or (if you’ve brave) an invitation to your house for a movie-and-popcorn or a seasonal arts-and-crafts afternoon.

Because I have a kiddo who does best knowing in advance about plans but then gets highly disappointed and obsesses about any cancellation, I also work hard at devising a potential easier-to-execute Plan B (and C), such as checking in with a close cousin or inviting Grandpa to lunch.

And then? I dream up ideas for the next mom-only vacation day. After all, I’ll need it to recover from the holiday play date pursuit.