Mr Thomas "Tom" Winslow is a childhood friend of the protagonist, along with Miss Earlwood and Miss Ingram. He is known for his frequent arguments with Miss Ingram, which stir up a ruckus in Darlington. He has recently returned from some time abroad with his parents.
As a child, Mr Winslow grew up with the protagonist, Mary and Phoebe, singing nursery songs, having picnics and attending dancing lessons together. Winslow later describes them as his oldest, closest and dearest friends. He has early memories of dancing the cotillon with Phoebe for the first time at Dunnistone's gardens. He also mentions being terrified of the protagonist's mother. Tom was later sent off to boarding school for several years.
Relationship with Miss Ingram
- “ I tell you, there must be something more in a marriage! A spark, a fire, a meeting of minds, a collision of temper and vivacity!”
- ― Mr Winslow to Mr Digby in The Assembly Rooms
It is unclear when Mr Winslow began to have particular feelings of affection towards Miss Ingram. After he returned from boarding school, Tom became, in his own words, insufferable towards Miss Ingram, probably marking the beginning of their tumultuous relationship which is characterised by frequent public rows involving an angry and upset Phoebe and an an amused Tom. Their concerned friends can see that this emerges from Tom's inability to express his feelings towards Phoebe in an appropriate manner.
Depending on the protagonist's advice at a country dance, Mr Winslow proposes to Miss Ingram either after an intimate picnic, as a public gesture during a ball at Dunnistone, or in some other unspecified way. Miss Ingram will always reject this first proposal. The success of Tom's second proposal depends partly on the advice given to him by the protagonist.
If Phoebe accepts Tom's proposal, the pair will be later seen together at the town centre. The mystery recipient of the numerous ladies' hats and dresses he purchases are also revealed to be Miss Ingram. The protagonist will also receive the Matchmaker achievement.
If Tom's proposal is rejected, the protagonist will observe a dispirited Tom staring at a regretful Phoebe at town. The hats and dresses Tom purchases will also be given to Phoebe, but as a wedding present in light of her engagement with Mr Brown.
Tom is well-liked for his cheery and mischievous nature, and his attraction to Phoebe comes partly from the spark in their relationship. He always has a smile on his face, and he is charming, flamboyant and good at flattery. His unpredictable character leads Miss Ingram to question their proposal, stating "Who knows what Tom might do in a year or two." Mr Winslow's sometimes childish behaviour and excessive attentions towards Miss Ingram is a source of contention from his friends and disapproval from older townspeople in Darlington. His pursuit of Miss Ingram does reveal that Tom can be thoughtful and sincere, as when he decides to take his childhood friends out on a quiet picnic.