Greetings,
I’m a big fan of your column and would like your insight on how to deal with a good friend of mine.

My friend, let’s call her Maude, is a wonderful friend: loyal, honest and kind. She is also incredibly introverted and rather socially awkward. It took me awhile to get to know her, but it was worth it.

Here’s the problem: despite being all things wonderful in a person, she really struggles in the romance department. I cannot stress how different she is as “good friend” versus “person seeking a boyfriend”. Although she is 30yrs old, I don’t believe she’s ever had a real boyfriend or serious relationship. As I learned from you, this is no big deal. The big deal that I don’t know quite how to address with her, is that she has behaviours that I can only describe as female incel. These are the entire reason she can’t seem to find a relationship.

Before I got to know Maude, I knew her mostly by reputation. A number of my guy friends had reported that she was a “stalker”. She will show up at places where she knows the object of her affection will be or at his place of employment and send dozens and dozens of texts asking for “closure” after casual sex or even mild flirtation with no physical contact. At first, I thought this gossip was just men being full of themselves or exaggerating her behaviour. It turns out that her reputation was well earned.

After a very long streak of abstinence after her “promiscuous phase” (her words, not mine), Maude decided she was ready to start dating again. Around the same time, a friend of mine had recently gotten out of a relationship. He’s good looking, smart and fun – however, he’s doing some post serious relationship tom catting around. In other words, he would be very fun to sleep with provided you did so with no expectation of a relationship. Surprisingly, Maude started hitting it off with him and really came out of her shell and they had some good conversations and went on one date several months ago. It ended in a hug. Since then, they’ve been sending flirty texts to each other in a kind of build up to a maybe sexual situation. Both of them confide in me, so without betraying each other’s confidences, I can say for certain he did have a genuine affection for her, but not as strong as hers for him.

Then the stalking and obsession started to kick in. He seemed to take it in stride, but he also is probably blissfully unaware of the behind the scenes work this woman does to get her man. She was getting irrationally upset and telling us girls about all these frustrations in this not even a relationship. This escalates over a few months and he naturally backs away as he’s been openly keeping time with a number of ladies. Finally, after a week of constant texts from her asking if she was being “crazy” for this and that and “should she send him another text” type bullshit, she went against all the ladies advice and sent him a missive about how she was very upset with him for “leading her on”. She was not led on. He handled it graciously, but backed off both the friendship and flirting. Since that fateful text, she’s been spiralling. All her social media posts are rather vague attempts to get his attention and she’s making a big deal about the few random dates she’s been on in an effort to make “him” jealous. In concert with her very awkward and public attempts to “date”, she has also gotten progressively militant about there being no available guys and making blanket statements about how men are only interested in looks etc. Long story long, she’s making herself miserable and inadvertently scaring away any man who might be interested in getting to know her. Also, her stalker reputation lingers, so that coupled with her introvertedness and bizarre takes on how relationships work is putting her in a pretty bad place.

I’d like to be understanding and want her to be happy, but her overall perception and approach to things are so far removed from my take on things that I don’t know how to remain supportive and provide useful feedback in a sensitive way. One can’t just say “well, you gotta stop this stalking and making up relationships in your head”. Should I just tell her to write you or do you have any ideas on how to gently wrangle her into healthier and more productive approaches to dating and sex?

Thanks in advance for any help you can provide here.

Friends In Need

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