Unwanted Attention from Other Adults

I think she should tell him precisely using "I statements" what he is doing that makes her uncomfortable and ask him to stop. " I feel very uncomfortable when you comment on my appearance. Please stop." She doesn't need to accuse him of hitting on her. He would likely deny it and then insult her in some way. Guys like that are on a power trip. It's all about him taking control and making her feel helpless. Of course, it's unpleasant to confront him. If I were her I'd practice in front of a mirror and with you or a friend. I think getting anyone else involved isn't necessary unless he is actually getting physical or saying overtly sexual things. But sounds like he's savvy, he's doing just as much as he thinks he can get away with, getting his thrill while not overstepping enough to get confronted. She needs to let him know clearly and calmly that it's not ok. If it progresses from there she can get other people involved. Sorry she is dealing with this unpleasant situation but think of all the other women she will be helping by calling this creep out. 

If she had already confronted him several times and the guy's behavior continued, trying to figure out who else to tell might be appropriate but at this point I think it would create a whole bunch of drama where it might not be necessary.  The first place to start when a guy is behaving this way is to assume the best of him (ie—he's not meaning to harass or power-trip, he's just flirting) and then to address it directly.  "Hey, guy, I'm not interested. I'm happily married. Please stop talking to me."  And then ignore all further comments by him. Behave as if he does not exist.  I have been hit on my entire life (as have most women) and I can assure you this approach works the majority of the time.

If it does not work and he continues to make inappropriate comments after this or if he escalates things, I'm less sure what to do (him being a cop does make it feel more tricky.) But maybe start with your wife just telling him to leave her alone.

Keep it simple, keep it clear, set a firm boundary to back off. Should be relatively easy unless it's mutual or being entertained in some fashion. Doesn't seem like a good fit for play dates unless arranged with the mom or grandmother, wouldn't recommend; too many other kids to play.

If your wife is that uncomfortable with his interactions or comments, best to shut down and stand clear or future actions could be misnterpreted. By the way, not saying something to him makes him thinks it's "Ok". With current climate and state of affairs surrounding Meetoo movement the silent must take responsibility and speak up, confront and smash any possible idea of harassment. Skirting around issue can lead to HUGE problems, drop the hammer now!

I don't have to "play nice" if I am feeling uncomfortable or violated!!!

Oh dear that sounds so uncomfortable. Still, I wouldn't be direct and say things like, "Stop hitting on me." Your children are going to be at the same school for a while, and possibly on the same sports teams, same extracurricular classes, so you don't want to create a very negative feeling with another parent if you might end up seeing them all the time for YEARS to come. Some things your wife might do: Drop off at a slightly different time, a little earlier, or really late so she can drop off and run. Drop off at a different location (kiss goodbye and ask your child to walk to the classroom by himself). Team up with another mom so they are always chatting busily with each other during drop off, with no room for someone to cut in on the conversation. Talk loudly on her phone during drop off and look busy. etc etc. Perhaps the other dad will get the hint, or just get bored and start talking to someone else. But if your wife feels it is progressing to the point of harassment or she might be in danger, then definitely talk to a school administrator about it. Oh, and please don't say things like "we'd like our kids to be friends." No no no. If the father makes your wife feel uncomfortable, then your kids cannot hang out. That's asking for trouble. Why make the situation worse? 

Your wife needs to be direct with this guy. He knows exactly what he's doing, and he's testing to see if he'll get strong pushback or if he can take this farther. The next time it happens, she should say something like, "Please don't make those kinds of comments. You've made several comments that make me uncomfortable on several occasions. Please stop." No doubt he'll be a jerk about it but he might stop. If he doesn't, then it will be time to escalate. I would probably speak to the school administration to see if there's anything they can do. If they can't, then perhaps speak to the grandmother. 

I'm sorry to say it, but I would avoid letting your kid develop a close friendship with the other child. I would never let my child have a play date at this man's house, for example. He sounds like a classic predator. 

I agree with Amomanon, except the phrase I'd use is: "I do not like you commenting on my appearance. Stop it now."  The " I feel very uncomfortable when you..." doesn't work among my tribe in Texas--too dadgum touchy feely-- and the 'please' is inappropriate: this isn't "Please bring me a cup of coffee" This is "Stop, you knucklehead!"   Also, what about walking away from him?  Ignoring him?  Yes, the kids...but are they standing there when he says these things? If yes, they need to see how she handles it & if no, then she can say/do whatever.  As Amomanon says: "...think of all the other women she will be helping...."

I suffered in silence for so long over this sort of thing.  Thank you for allowing us to help you/her and even him.

Nothing  you describe is particularly out-of-bounds, and yet your wife is clearly creeped out.  Maybe he's clueless, or a guy on the make, or maybe there's more.  But right now you don't know enough.

First, I think you and she need to parse this out.  What is she sensing about him that is upping her anxiety meter?  Is there an underlying sense of something "not right", or violent, or stalker-like?  Or does she just feel he's a disgusting letch?  If she can name what it is about him that is bothering her, that's a step towards figuring out how to handle it. 

Secondly, brainstorm some ideas.  Can she get another parent to come with her or to handle drop-offs for her?  Go a little earlier or later?  Not get out of the car so there's little chance to talk?  I realize all of these are inconvenient and put the burden on her to cope with his misbehavior, which isn't fair.

Third, you say he's an ex-cop.  Do some research on him and his background.  What you describe sounds like a man who's divorced or widowed.  Any history of bad behavior on or off the job?  Restraining orders? Is he affiliated with your local police station? And carefully ask around, speaking with neighbors you trust to be discreet, to see if other women have gotten weird vibes from him.  And she should start keeping a log, detailing what happens day by day and her reactions.

If she feels that he could present a threat, you or she can then contact some experts on stalking and rape .  
Here are places to start:
http://victimsofcrime.org/our-programs/stalking-resource-center
http://victimsofcrime.org/our-programs/stalking-resource-center/help-for-victims/stalking-safety-planning
https://www.rainn.org/safety-prevention

Fourth, she needs to check in with her "good girl" training and see if she wants to or needs to modify her behavior.  It's generally ingrained into women that we should be "nice" in social settings and not make other people uncomfortable, so perhaps up to now she has not felt comfortable with "go away" body signals.  Can she find ways to politely freeze him out?  I'm not suggesting direct rudeness, but putting up an emotional wall, avoiding smiling and eye contact, answering tersely or not at all, declining coffee invites without excuses, etc.  The idea is to be appropriate but distant, not to let him feed off her emotions.

What I DON'T recommend is pretending to agree to do coffee, and then "not following up." If he has stalker tendencies, you do not want to give any indication that his attentions are welcome.  I can't think that grandma or teachers might be any help, although possibly the principal might be (but do your homework first.) 

 I also think that you directly accusing him of hitting on her might not be the right move, because handling direct confrontation is a cop's specialty.  It's better to ask him to stop a specific unwelcome behavior than to accuse him of intentions that can easily be denied, and which certainly aren't illegal.

The previous poster is spot on with advice and what’s going on with that father. He knows exactly what he’s doing (controlling and preying on those that will not speak up) and enjoys making your wife uncomfortable. Your wife needs to confront him, be assertive, and say what previous poster suggested using “I”, “I feel uncomfortable when you comment on my appearance. Please stop.” His response will be to deny it and insult your wife in some way. He will think he’s not the problem but that your wife is the problem. However, by having your wife be assertive and standing up to him, he will get the message that she will stand up for herself and that he can’t prey on her. If it makes her more comfortable, perhaps she can make that statement within hearing distance of an adult witness. 

For jerks like him, your wife should not bother being nice and talk about getting coffee with the spouses. That just opens more doors and opportunities for him to harass and bully her. I would recommend minimizing contact, don’t involve his mother (she’s probably an enabler), and steer clear of him.

Is your wife a nice, happy, friendly person? I ask because I'm not, and unlike some of the other posters here, I don't get hit on.  You have to be willing to stare coldly without smiling when a man talks to you, and either say NOTHING in response to what they are saying, or say things like "I'm busy right now," or "I don't want to talk."  Or look past him, and take out your phone and do something with it.  Without smiling, without apologizing. He'll mutter "bitch" but guess what, he'll give up and go elsewhere. 

Yes, this borders on "rude." Personally, I think it is totally fine to be rude. His attentions -- which he knows perfectly well are unwanted - - are extremely rude.  He's just taking advantage of her politeness to gratify himself. &K*# that.  

This guy could be hitting on her, he may be trying to be nice, or he may be a creep. Since it sounds like your wife hasn't ever told him she doesn't like his compliments, I'd hold off on the creep judgement until she's up front about that. The next time this happens, SHE should say to him "Your comments about my appearance (or other description of his behavior that she doesn't like) make me uncomfortable and I don't like it. Please stop." She can absolutely - even preferably! - do this in front of his and your child. Respectfully, politely, firmly, and directly advocating for herself would be a great example to the children on how to handle things that may seem ok/borderline but that you still don't like. IF the behavior continues, then SHE should escalate (not you)- directly and firmly tell him that his comment is inappropriate and she will not tolerate any more, and she can add whatever her next step will be, such as reporting the behavior to the school or police. She has the power and the right to stand up for herself .

I think it's a great idea to model these conversations in front of your children (and talk to them later about why you did what you did- What made you uncomfortable, how you chose to handle it, and how your child can handle it when someone does something to make her uncomfortable, etc.). This is a great learning experience/teachable moment for your and his child. Think of it that way. One day, when someone says something that makes her uncomfortable, which will absolutely happen many times, how should she respond? And keep in mind, the person making her uncomfortable could be a major creep or predator, or the super sweet but maybe a little nerdy or shy kid in class who just worked up the courage to say something nice to his crush. Either way, she has the right and should respectfully and directly call out what makes her uncomfortable, then escalate and get help if that doesn't work.

I would be polite and quiet but direct.  "Perhaps you don't mean anything by it when you say such things, but it makes me uncomfortable.  Please stop."  Any kind person with good intentions will probably be taken back but respond with an immediate behavior change.  If he gets rude or ups his game, then you know better what you are dealing with.  I definitely would not lead him on with the promise of coffee even if spouses are mentioned.  Write a detailed account of what has happened thus far.  Document when she confronts him and exactly what interaction takes place.  Document anything the occurs later.

You said it in your own question - this perpetuates when we don't talk.  Many responses have said that she should explicitly tell him to back off.  That is sometimes easier said than done.  If she can, great.  If not, another strategy would be to talk to some of the other moms there about what is going on and enlist their help.  Does she have some other mom friends?  Could she ask some other moms if this has ever happened to them, or if they would be willing to hang with her at drop off sometimes, even just to observe the interaction with this dad and see what they think.  Sort of as a witness.  One thing we learned from "me too"  is that many women think they are the ONLY one and that stops them from talking, but often, there are several people receiving the same treatment.  It can be empowering to find you aren't alone - and other women often are willing to help, as we have all been there.  Just another suggestion.

I am extremely disheartened by the number of replies I see excusing this behavior. One person actually blamed the #metoo movement for making people misconstrue simple flirting. Listen, I'm going to say this here, and I'm going to keep saying it until the patriarchy crumbles: There is a gap the size of the Grand Canyon between flirting and harassment, and when you conflate the two, you are part of the problem. 

In addition, blaming this woman because she might be "friendly and nice," and saying that a woman only need to respond with a firm "stop it, I don't like it" is an absolutely false and dangerous assertion. If you do this with the wrong guy, you will absolutely get followed home as he screams at you for being such a b* and not having a sense of humor, etc etc etc. I'm so glad you PERSONALLY have had the experience of your firmness being enough, but that is not true across the board. This woman is already second-guessing her work outfits. Then she's told "oh, it's because you're a pleasant person, stop being so pleasant." Please understand that being more rude, more pleasant, more ANYTHING does not change the outcome. 

To the OP: I would suggest arranging with your work that you do the commute for a month. Do not confront this person directly. Do not ask directly if he is hitting on her - he will just deny it and act aggrieved, and then bring it up next time he sees her: "I heard you thought I was hitting on you!" Just get out of his purview. A discussion at school will blow up. 

I just listened to the episode of This American Life about five women connected to the guy who runs Alternet. His wife/partner said she knew he was "a flirt," and that he needed that kind of interaction to puff up his ego, and that she would smile at women he was flirting with as a "oh well, boys will be boys" kind of salute. She regrets it now. Because the flirting was just the top layer. I recommend a listen. 

I LOVE to flirt. I HATE to be harassed. There is so much difference between the two. Please, spend some time thinking about this. 

Just to clarify--most of the posters who suggested being "less pleasant" or even "rude" were not excusing this man's behavior and were not even remotely suggesting that the OP's wife is somehow responsible for being harassed. We're all just spit-balling options that may change the situation.

Harassment is like bullying--the victim doesn't cause it, but needs to find a safe way to stop it.  You suggest de-escalating by changing her schedule.  That may or may not work but it's a major inconvenience for her. OTOH, if she can make social interactions a dead end, he's more likely to move on.  If she can be "rude" enough to ignore his social cues and compliments, she takes energy away from the interaction.  Freezing the harasser out is a good way to communicate that he's not the one who sets the agenda.