My family is good friends with our next door neighbors. She’s a single mom with a son the same age as ours. She had just gotten a divorce from an abusive relationship when she moved in next door several years ago. Recently, she told us she was considering putting herself ‘back on the market’ and possibly start dating again. I mention the abusive relationship because she projects a certain traumatized air when it comes to even talking about relationships. Like, any mention of the subject is usually an invitation for her to relate an anecdote how her ex used to say horrible things to her and engage in sociopathic behavior. She’s an introvert, keeps very much to herself, and gather she has no other IRL friends she interacts with, apart from us. She also has been diagnosed with Generalized Anxiety Disorder and is being treated for the condition.
Here’s the thing, she’s hinted on two occasions now that perhaps my wife and I would like to accompany her on a double date when she finally does make a date. We really didn’t know what to say and have remained non-committal. On the one hand, I think we understand her impulse to want to feel safe because of her horrible experiences in the past dealing with men. She’s insecurity incarnate, and since we seem to be the only people she trusts, it makes sense that she might want us around in what she perceives to be a potentially dangerous situation. On the other hand, It’s kind of weird; she’s in her late 30’s and we’re a married couple in our mid 50’s, and I get the impression she may really be looking for chaperones as well as social lubricant. I confess I haven’t heard of anyone signing up for an online dating service and then setting up a double date with a married couple to accompany.
I don’t know, maybe I don’t get around enough myself and perhaps this arrangement isn’t as unusual as it strikes me. Part of me wants to say ‘are you SURE you’re actually ready to start dating?’ As additional detail, she ended up marrying shortly after high school and has next to zero experience with dating in general.
I don’t mind helping her out, but I’m not sure our presence would actually be all that helpful from a dating standpoint. Would you go on a double date, or is there a more effective way to help her out here?
First up, I think you should ask her why she wants you along. Once you know that, then you can work on whatever the issue is. If it’s safety, there are ways of handling it that don’t involve you sitting at the table with her and her date.
I think her date would find it pretty weird if you came along. I suspect that a lot of guys will bail just because of that alone. You might present it to her that way. Tell her that a first date is for them to get to know each other and that if you’re there, it will make the situation more awkward and he may be less likely to want to continue dating. I could maybe see it being okay if you were the same age, but it’s going to be weird all around with the age difference.
You should probably tell her that dating is a process where she’ll find people she is interested in. From your description, I have a feeling she’ll latch onto the first guy she meets and then try to make it work no matter what. Instead, she should get to know a lot of guys so that she finds a guy who she’s compatible with.
The second time she dropped the hint I asked her why she’d want some ‘old fogeys’ like us going along and cramping her style. Her response: “Oh, you wouldn’t cramp my style. I’d actually feel more comfortable on a date having you guys along.”
I was kind of surprised she’d mentioned this notion a second time and didn’t delve for details at the time what she thought ‘comfortable’ entails. I took it to mean both safety and also emotional support, although I could be wrong on that.
In your posts, you come across as a sincerely nice guy. Many people claim to have good friendships w/ their neighbors, and I hope you do as well.
My personal preference, tho, is to not get TOO close to my neighbors. Not to be too dramatic, but in the event things go sideways, there is no getting away from them. We pretty much make an intentional effort to establish and maintain what we call “Hey neighbor!” status. You know - when you see each other, you smile and say, “Hey!” Offer to put their trash cans out if they are on vacation, maybe lend a tool or 2, chat over the fence while doing yard work… But anything more than that has potential risks which might outweigh any benefits.
I appreciate your wanting to help out this person, but do you think there is a risk of her blaming YOU should anything turn out badly? She sounds like she tends towards the needy end of the spectrum. Do you and your wife really want to hear all the twists and turns of her sating life?
If you DO decide to do this sort of thing, I’d suggest it be more of a “group of people doing something” thing, rather than a “date.” And maybe if she progresses to having a date over for drinks/dinner, she might invite you as well.
But she is an adult. At some point, she is going to have to fly solo in this - and other - respects. Think carefully before making her problems yours.
It’s interesting that with relatively little information you made the same conclusion as my wife did concerning her ‘making it work no matter what’. It may be her underlying insecurity, but for some reason she exudes an almost desperate ‘please please like me, I’ll do anything on earth for you if you would just accept me’ vibe. She has very low self esteem and self confidence, and may think she can’t pull it off herself without our ‘assistance’. We’ve already crossed the threshold to being de facto ‘counsellors’ with her on more than one occasion. And yes, she has a therapist she sees every week or two. When this has happened in the past we’ve recommended she talk to her about the things that are bothering her. Maybe this is one of those times.
Just a suggestion, as I’m also not sure she sounds ready to date at all, but how about something like going to the same restaurant at the same time. Being in the same place, so within calling distance if she gets freaked out and doesn’t know how to handle it, but at the same time not listening in and certainly not being a double date? It might help her feel safe, without putting any responsibility to evaluate her date on you guys, or weirding her date out.