April 1660
Dines with Lord Sandwich and discusses political matters.
May 1660
Present in the fleet; Pepys notes his involvement in the celebrations and council of war.
June 1660
Accompanies Lord Sandwich to Trinity House for entertainment.
July 1660
Attends Navy Office meetings and is suspected of scheming over lodgings.
August 1660
Attends the office with Pepys and travels with him to the Admiralty.
September 1660
Accompanies Pepys to the Committee of Parliament regarding Navy debts.
October 1660
Accompanies Pepys to Whitehall and Deptford; shares merry discourse and bawdy songs.
November 1660
Travels with Pepys and Batten; sups at Batten's house.
December 1660
Present at Woolwich and at a dinner where he becomes very drunk; Pepys leads him home.
January 1660–61
Navy officer; Pepys visits him and socializes with his family.
February 1660–61
Visits Pepys in the evening, accompanies him to Court, and joins in Valentine celebrations.
March 1660–61
Attends meetings with Pepys, teaches Coventry about Jamaica, joins in dancing.
April 1661
Naval colleague; dines with Pepys, drinks with him, and joins the coronation viewing party.
May 1661
Accompanies Pepys to Walthamstowe for the christening; discusses naval matters and past politics.
June 1661
Accompanies Pepys to Woolwich and Deptford, and later joins him for a late-night drinking session.
July 1661
Visits Pepys's home on a Sunday; his daughter arrives from Ireland.
August 1661
Sir W. Penn; accompanies Pepys to Walthamstow, carries Pepys to Paul's, and is the target of a counterfeit letter from Pepys about a stolen tankard.
September 1661
Participates in the tankard prank; dines with Pepys and attends plays.
October 1661
Accompanies Pepys to Whitehall and to the Dolphin tavern; discusses reluctance to attend Lord Mayor's feast.
November 1661
Naval colleague; dines and travels with Pepys, and accompanies him to Westminster and the theatre.
December 1661
Naval colleague; dines with Pepys, plays cards, and accompanies him to Moorfields and the Treasury office.
January 1661–62
Travels with Pepys, discusses his son's education, and hosts supper.
February 1661–62
Walks with Pepys in the garden, dines with him, and discusses office mismanagement.
March 1661–62
Naval colleague; joins Pepys in walks, office work, and discussions about house repairs.
April 1662
Naval colleague; accompanies Pepys to Portsmouth and shares in pay and social activities.
May 1662
Travels with Pepys from Portsmouth, has a tense exchange about confidence, and is threatened by Sir G. Carteret over Mr. Coventry's appointment.
June 1662
Pepys accuses Penn of acting like a 'base raskall' in a dispute over contract duties at the Navy Office.
July 1662
Also involved in paying off the Royal James; Pepys dines at his house.
September 1662
Accompanies Pepys to St. James's and discusses lodgings and servant issues.
October 1662
Sick and in great pain; Pepys visits him.
December 1662
Neighbor; Pepys visits him briefly on Christmas Day.
January 1662–63
Reported ill again; Pepys visits him briefly.
March 1662–63
Pepys opposes his patent to assist Sir J. Minnes and later clashes with Captain Holmes.
August 1663
Pepys visits him while he is lame; discusses sending soldiers to Ireland.
September 1663
Meets with Pepys at the office; visits Pepys's home with his daughter.
October 1663
Discussed Sir J. Minnes and Sir W. Batten with Pepys.
November 1663
Attends church for the first time in months after illness; later gives Pepys a ride home.
February 1663–64
Mentioned as giving a horse to the Duke of York, later given away to a Frenchman.
March 1663–64
Mentioned as the other seaman in Parliament.
May 1664
Dines with Pepys at the Leg tavern.
August 1664
Attends office meetings; his brother dies; offers coach to Epsom; buries brother under communion table.
October 1664
To go in the same ship with the Duke; Pepys grudge him the honor.
December 1664
Pepys visits him and notes his dissembled respect and love.
January 1664–65
Gives Pepys a ride to Whitehall; present at Sir W. Batten's with disordered talk.
March 1664–65
Reported to have carried himself disrespectfully to Lord Sandwich at sea.
September 1665
Walks with Pepys and discusses observations of France; disputes the meaning of a French song phrase.
October 1665
Found in bed at Hill-house; Pepys distrusts him but secures his consent to move silk.
March 1665–66
Pepys notes Penn becoming more supple; they discuss payment of Cocke's bill.
May 1666
Goes down to the Fleet; Pepys fears being summoned to inform him.
June 1666
Penn travels with Pepys to Whitehall and is commanded to go to Harwich to dispatch ships.
July 1666
Returns to town; Pepys dines with him and his family, noting the necessity of keeping in with him due to his praised service at Sheerness.
August 1666
Detains Pepys with public business, accompanies him to Lord Bellasses, and shares news about the King's house reopening.
September 1666
Penn walks with Pepys in the garden, discussing timber trade and privateering opportunities.
October 1666
Accompanies Pepys to Whitehall and the Committee; departs to join the fleet at the Nore.
December 1666
Pepys borrows his coach for the christening outing.
January 1666–67
Hosts a dinner and attends Pepys's feast, showing some envy at Pepys's plenty.
February 1666–67
Hosts a poor wedding dinner for his daughter; clashes with Lord Brouncker over examination methods; rants after Brouncker leaves the office.
March 1666–67
Brings an order from the Duke of York for a fireship and acts cunningly during the Carcasse dispute.
April 1667
Mentioned in gossip about his family's poor household management despite outward show.
May 1667
Navy Board colleague; participates in the Carcasse report review.
June 1667
Naval commissioner; accompanies Pepys to Whitehall and discusses the fleet's financial difficulties.
July 1667
Attends office meetings and discusses the chain's break with Pepys.
August 1667
Dines with Pepys and accompanies him to the playhouse and St. James's.
September 1667
Present at Batten's dinner; his family's sluttishness is discussed.
October 1667
Suffering from gout; involved in Parliamentary proceedings and discussions about the fleet.
November 1667
Walks with Pepys and discusses the likelihood of the Houses failing to agree after their free conference.
February 1667–68
Exchanges high words with Pepys at the Board; later attends the play with Pepys and Lord Brouncker.
March 1667–68
Accompanies Pepys to Whitehall and Hyde Park; rumored to command the summer fleet.
May 1668
Labours to have his impeachment answer read; discusses Parliament with Pepys.
September 1668
Attends Treasury meeting with Pepys and Brouncker; later sups with Pepys.
October 1668
Pepys speaks with him about Mr. Hater's place; later they attend a play together.
November 1668
Penn is rumored to have resigned his Navy Office place to become a partner with Gawden in the Victualling; Pepys is glad of his departure.
April 1669
Hosts a dinner for Pepys and others; Pepys is little pleased with the host.
