September 26, 2021

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My sister is dating her boss – Love Letters.com – Boston.com – Boston.com – Boston.com

Hi Meredith, My sister has had a decently messy love life for many years. She's very insecure abo.......

Hi Meredith,

My sister has had a decently messy love life for many years. She’s very insecure about herself, her relationships with others, the way she looks, etc., and it shows in her relationships. She’s very kind, but she has commitment issues and will fling herself at any person who shows her a modicum of kindness or attention. She cycles through close friends and cheats on every person she dates. She’s been in therapy for years and has discussed all of this with her therapist. We’re very close and she trusts me to be honest with her about her decisions. I try not to be judgmental and let her work through her issues, only offering advice when asked.

Well, now she’s dating her boss who is 15 years her senior. She’s told me about how she’s very open with her feelings and struggles at work, whether it comes to her strained relationship with her ex, our parents (she recently moved out of their house) or friends. I think it’s inappropriate, but apparently it’s very normal(?) at their office. This guy she is now seeing has three very young kids. She confessed her feelings to him while he was still married and seemingly had no intentions of getting a divorce. But in the few weeks since then, he has moved out, filed for divorce, and is fully dating my sister. He’s 40! And she expressed in recent months, pre-relationship, that she doesn’t want children and felt pressured by our …….

Source: https://loveletters.boston.com/2021/08/sister-dating-boss.html