Henry's first trip back to Clare's childhood
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When Clare and Henry meet for the first time, Henry does not know Clare. Although she has had years of visits from Henry, he has yet to travel back to her childhood.

In fact, it is several years before Henry begins his visits back to the Meadow. This is an interesting situation as Clare has a ton of memories of Henry's visits, and he has absolutely none. See the March 1994 listing below for more details.

October 26 1991 Page: 4Alba: Clare: 20Henry: 28
Henry meets Clare, in real-time.
Henry says that he has never met someone from his future before, meaning he's never met anyone in real-time who, in their past, met a future version of himself. Obviously Henry himself has seen his future self many times. When Henry meets Alba for the first time, she has seen his future self in her past, but this does not occur for him in real-time, Henry travels to the future. Other than this meeting with Clare, there are no other examples of this type of encounter.
After October 26, 1991 Page: ixAlba: Clare: Henry: ?
Henry travels back to 1976, watches 13-year-old self mow his Grandparent's lawn.
All we know is that Henry is with Clare when he makes this trip back. It could be any time between when he meets Clare and his death in 2001.
November 28 1991 Page: 231Alba: Clare: Henry: 28
Henry travels back "around Thanksgiving" to December 24 1969 and witnesses his mother's death
November 30 1991 Page: 129Alba: Clare: 20Henry: 28
Dinner party with Charisse and Gomez. Gomez warns Clare about Henry.
December 14 1991 Page: 137Alba: Clare: Henry:
Henry 36 from May 9 2000 arrives and meets Gomez in the alley.
Weird Gomez moment #2

See May 9 2000 for details on this strange meeting.
December 15 1991 Page: 146Alba: Clare: 20Henry:
Gomez talks to Clare about meeting future Henry
December 22 1991 Page: 151Alba: Clare: 20Henry: 28
Clare and Henry see Henry 33 from November 13 1996
First Henry arrives at Henry's apartment, then Clare meets him while she and Henry are at Violent Femmes concert
December 24 1991 Page: 163Alba: Clare: 20Henry: 28
Clare takes Henry to Meadowlark House for Christmas
This is interesting as, just before dinner, Clare takes him to see the Meadow. This is Henry's first trip to the Meadow. He's never been there before.
December 24 1991 Page: 195Alba: Clare: Henry: 28
Henry disappears from church, travels back to an elementary school.
December 28 1991 Page: 196Alba: Clare: Henry: 28
Henry 28 arrives in his own apartment sees Henry 28.
Henry disappeared on Christmas day from the church, travelled back to time unknown and appeared in an elementary school. From there he disappeared and showed up here.
1992 Page: 57Alba: Clare: Henry: 28
Henry travels back to February 1969, visits Henry 15, talks about determinism
May 9 1992 Page: 219Alba: Clare: Henry: 28
Henry visits his father and Kimy
May 24 1992 Page: 228Alba: Clare: 21Henry: 28
Clare's 21st birthday and Henry's marriage proposal
May 31 1992 Page: 233Alba: Clare:21 Henry: 28
Henry takes Clare to meet his father and Kimy
June 10 1992 Page: 241Alba: Clare: 21Henry:
Celia approaches Clare in a café
September 5 1993 Page: 247Alba: Clare: 22Henry: 30
Henry and Clare talk about drugs for his condition
This is interesting as there is nothing mentioned between June 10 1992 and September 5 1993. 15 months with nothing.

Also, Henry proposes in May of 1992 but they don't get married until October 1993. Why the 18 month engagement? As this is the first we hear is about Henry taking drugs we might assume that he has been travelling a lot, but we don't hear any details.
September 6 1993 Page: 250Alba: Clare: Henry: 30
At Ben's apartment Henry runs into Gomez
September 27 1993 Page: 259Alba: Clare: 22Henry: 30
Clare finds Henry after adverse drug reaction
October 22 1993 Page: 262Alba: Clare: Henry: 30
Henry gets his hair cut
October 23 1993 Page: 274Alba: Clare: Henry: 30
Henry travels back to June 13, 1976 misses wedding ceremony.
October 23 1993 Page: 271Alba: Clare: 22Henry:
Henry 38 from 2002 arrives, stands-in for Henry and "marries" Clare.
October 25 1993 Page: 279Alba: Clare: 22Henry: 30
City hall wedding
January 2 1994 Page: 489Alba: Clare: Henry:
Henry 43 from December 18 2006 arrives, sees Ingrid's suicide
March 1994 Page: 285Alba: Clare: 22Henry:
Clare waiting for Henry to tell her he has traveled back to see her as child, it hasn't happened yet.
In March 1994 Clare states that Henry has not yet travelled back to see her as a child. We know that Clare's recollection is that Henry's first trip back was when she was 10. He kept saying "Oh god" and was bothered by his nudity.

We know that when Henry is 32 he travels back to 1987 and goes to the party with Clare 16. This incident could have been as early as June 16, 1995 when Henry turned 32. We know that on July 12 1995 Henry travels back to 1987 to help Clare 16 get revenge on Jason. We know that neither of these were Henry's first trip back to see Clare.

In fact, on both these trips, Henry is pretty composed. It would appear that he is now comfortable popping in at odd times in Clare's childhood. Therefore the first trip back was probably quite a while earlier.

It is disappointing and odd that we do not hear of this first trip for Henry. Obviously for him its a big deal as Clare fell in love with him because of the childhood meetings that he has yet to experience. For Clare, she and Henry now have real-time shared memories, but most of her shared memories with Henry are from her childhood and real-time Henry does not share them yet. This is why Clare is waiting for Henry to tell her he has begun returning to their past. Given the importance of this event, its surprising that we do not hear about it.
March 1994 - June 1995 Page: 8Alba: Clare: Henry: 30-32
Henry travels back to 1981 - 1982 and visits Clare age 10. This is his first trip back to her childhood.