Maine woman sues landlord. Then came the drunk text asking her out: ‘My treat, of course’

A Portland, Maine renter says a dispute over lease renewal and rent control violations escalated into a yearlong legal process that ultimately resulted in a payout ordered through city enforcement, followed by what she described as an unexpected “drunk text” from her former landlord.

The account was shared by TikTok creator Margaret Skiff, who recently detailed her experience moving out of a Portland apartment in early 2025 after her landlord declined to renew her lease and later re-listed the unit at a significantly higher rent.

Skiff inquired about month-to-month

Skiff said she initially reached out to her landlord to ask whether she could remain on a month-to-month basis after her lease ended. She says she was instead informed her lease would not be renewed and that she would need to vacate within a few months.

From there, she reviewed local housing rules and reported concerns to Portland housing officials. According to Skiff, city officials found multiple issues, including insufficient notice and rent registration discrepancies.

Under Portland, Maine, rental regulations, landlords are generally required to provide extended notice periods for non-renewals and comply with local rent control rules tied to registration and allowable increases. City housing authorities can investigate complaints and order restitution when violations are found.

Skiff said officials determined she should have been paying a lower monthly rent than she had been charged under Maine’s rent control laws, and that she was also entitled to compensation for the improper lease termination.

The case ultimately led to a city-ordered reimbursement for months of rent overpayments, along with an additional penalty for the landlord’s failure to provide proper notice of the lease termination, according to her version of the story.

Then came the texts

While the legal process unfolded, Skiff moved out and requested the return of her security deposit. That is when she says the situation took an unexpected turn.

About a week after moving out, she followed up with her landlord about her deposit. He responded that he needed time to inspect the unit. Later, Skiff says she received messages indicating the apartment looked fine and that he would send $2,000.

Then, according to her retelling, the tone shifted. She says the landlord later texted her referencing a Portland restaurant before continuing to message her into the night. He allegedly wrote that he was planning to go to a steak restaurant and added, “Please let me know by noon if you would like to meet me there. My treat, of course.” Skiff, who said she had never met the landlord in person, declined.

The next morning, she says she woke up to an unsolicited 7 a.m. picture of the landlord with several younger men, followed later by an apology message. “Apologies. Was drunk texting. Sorry. Coffee, if you wish, sometime?”

Skiff said she did not respond. Skiff says the city ultimately closed the case after the landlord complied with the repayment order, though the process took about a year — no word yet on whether he continues to ask out his former tenants.