The question is a little flawed, in that both Armenia and Georgia both have had serious issues with becoming democratic, and strong arguments could be made that neither are fully democratic states. This question is also limited in that a fuller explanation requires violating the 20-year rule of the sub, so I will be focusing on events prior to 2002. This is important to note, as it means I can't speak about the 2003 Rose Revolution in Georgia, which is seen as the first real effort to democratize the country, or the 2015 Armenian protests, which are also the first real steps towards democracy there.

Both Armenia and Georgia were among the first of the Soviet republics to try and break free from the USSR as it began to collapse, and while the timeline is similar for both, it was for completely different reasons:

Armenia was dealing with trying to incorporate the Nagorno-Karabakh Autonomous Republic (an ethnically Armenian region that was part of the Azerbaijani SSR), which in February 1988 made an official request to leave Azerbaijan. This was opposed by Azerbaijan, and protests led to attacks which ultimately led to the start of the Nagorno-Karabakh conflict (see below for more). In December 1988 Armenia was also hit by a massive 6.8 earthquake. Anywhere from 25,000 to 50,000 people died, and caused billions in damages. The weak response from the Soviet government also led many Armenians to become further disillusioned with the Union, and further solidified the desire for independence.

The developing conflict with Azerbaijan led Armenia to declare in August 1990 that Armenian laws had precedence over Soviet ones; full independence was declared in September 1991, though the war was fully going at this point. Levon Ter-Petrosyan, a historian (he specialized in ancient Mesopotamia, or something like that) and a major leader in the independence movement, was elected the first president with some 83%. The war was halted with a ceasefire in 1994, and Ter-Petrosyan was re-elected in 1996 with a much more narrower 51%, though he was accused of rigging this and saw large protests. He resigned in 1998 due to his attempts to negotiate an end to the war, and was succeeded by the former leader of Nagorno-Karabakh, Robert Kocharyan, who had served a major role in the war.

Kocharyan’s prime minister was assassinated in 1999 during an attack on the Armenian parliament; there is some who believe he was behind the attack, as he used the aftermath to consolidate power further. The conflict over Karabakh loomed over Armenia during this time, and Kocharyan and his successor, his prime minister Serzh Sargsyan, put more emphasis on that than on further developing democracy in Armenia. Their party affiliate, the Republican Party of Armenia, had a monopoly on power until 2018, when it was ousted after popular protests brought to power the current prime minister (the political system was changed in 2015), Nikol Pashinyan, to power (who’s faced his own challenges, but beyond the score here).

In Georgia, there had been increasing pro-independence demonstrations, led by Zviad Gamsakhurdia and Merab Kostova. In April 1989 one demonstration was violently supressed by Soviet forces, and around 20 people died (mostly young women). This effectively ended any support for the Soviet government in Georgia, which was always tenuous to begin with, and later that year the Georgian parliament had effectively ignored Soviet direction. Georgia also had ethnic strife to deal with, in the South Ossetia Autonomous Oblast (a lower administrative designation than republic in the USSR’s hierarchy). The Ossetians are ethnically related to Iranians, and speak a language related to Iranian, and are historically relatively new to the Caucasus (most historians would agree they arrived around the 13/14th century, while some nationalist Georgian historians argue as recently as the 18th century). Compounding the issue was that directly north of this Oblast was the North Ossetia Autonomous Republic, which was part of Russia (the regions were connected by a 3.7km Roki Tunnel, built in the 1960s). In December 1989 the South Ossetian parliament issued a call for unification with North Ossetia, which meant joining Russia. This was vehemently opposed by the Georgians, who were led by Gamsakhurdia, a virulent nationalist, and the very next day the Georgian parliament abolished the autonomy of South Ossetia. This caused further tension, and led to war in 1991, which lasted until 1992.

In April 1991 the Georgian parliament voted for independence, and Gamsakhurdia was elected the first president. As noted he was openly a Georgian nationalist, and was reported to have said “Georgia for the Georgians”; while this was never confirmed, in a country with roughly 35% of the population being non-Georgian, it did not help. His actions in South Ossetia were not popular, and several local militias were formed as a result. By November 1991 the capital Tbilisi was under siege, and in January 1992 Gamsakhurdia fled to his home region of Samegrelo, in the northwest of Georgia, just south of Abkhazia, an autonomous republic. A military committee took control of Georgia, led by the militia leaders (notably Ioseb Joseliani and his Mkhedroni), though they soon invited the former Communist leader of Georgia and Soviet foreign minister, Eduard Shevardnadze to take up the role. He did so, leaving the militia to fight Gamsakhurdia, who was consolidating forces. The proximity of fighting to Abkhazia led that region to declare independence in 1992 (the Abkhaz are ethnically related to the Circassians and other peoples of the Northwest Caucasus, and not the Georgians. They also are indigenous to the region, though some Georgian historians dispute that). Despite fighting Gamsakhurdia still, Shevardnadze led an invasion into Abkhazia, which quickly turned into yet another war, which lasted until 1993 when the Georgians were forced to evacuate.

Gamsakhurdia himself also lost in 1993, and fled to Chechnya (which was not yet a battleground of its own). He returned soon after but died in December 1993 in unclear circumstances (some say suicide, some say assassination). With him gone Shevardnadze was clear to become the head of Georgia (he adopted the title president in 1995). However the militias were still around, and would not be dispersed until 1995 when Shevardnadze was able to consolidate his power, and had the militia leaders imprisoned.

Shevardnadze was a classic Communist leader and maintained power through corruption and nepotism. The first two elections he ran in, 1995 and 2000, saw him win with 77% and 82% of the vote (granted his main challenger was also a former Georgian Communist leader), and there was no question that the votes were not free or fair. When he tried to do the same in the 2003 legislative elections the opposition had enough, and this saw the Rose Revolution begin, which led to his ouster and the first real democratic era in Georgian history under his successor Mikheil Saakashvili (who is now in prison himself and being tried by the Georgian courts for abuse of authority).

The overreaching theme here is that like most post-Soviet states, Armenia and Georgia were dealing with a lot of turmoil in the 1990s, so while democracy was a stated goal, it took second place behind open conflict and efforts to develop a capitalist economy. And even now with relatively free elections in both states, they are still far from fully free and fair as the locals would like, though I will agree they are in a lot better shape than Azerbaijan (which also had its own eventful post-Soviet developments before the Aliyev family took over).

If you’d like to learn more, I would suggest the following:

General overview:

• The Caucasus: An Introduction by Thomas de Waal (2010; second edition 2018). I haven't read the second edition, but the first one is a great introduction, and de Waal is an expert on the region.

• The Ghost of Freedom: A History of the Caucasus by Charles King (2009). Similar to de Waal's book, in that they both start from the Russian conquest circa 1800. This is a more survey than introduction though, but still easily accessible.

Georgia:

• The Making of the Georgian Nation by Ronald Grigor Suny (1988; updated 1994). The updated version was written right after the civil war so gets into that a bit, but also dives into the full history of Georgia.

• Edge of Empires: A History of Georgia by Donald Rayfield (2012). With an extra decade of hindsight on Suny, Rayfield is able to cover the Shevardnadze era in detail, and the rise of Saakashvili.

• Georgia: A Political History Since Independence by Stephen Jones (2012). The name is fairly self-explanitory.

• Georgia from National Awakening to Rose Revolution: Delayed Transition in the Former Soviet Union by Jonathan Wheatley (2005). Wheatley looks at the political situation of Georgia from the Soviet era to the Rose Revolution, and how it got to that point.

Armenia:

• Looking toward Ararat: Armenia in Modern History by Ronald Grigor Suny (1993), again it came out right after the fall of the Soviet Union, but it looks at some of the background issues.

• Black Garden: Armenia and Azerbaijan Through Peace and War by Thomas de Waal (2003). A really great book on the conflict, which also covers the Armenian political situation until that point.

• Armenia and Azerbaijan: Anatomy of a Rivalry by Laurence Broers (2021). I will admit I have not read this yet, but am familiar with Broers' work, and would expect it to be a solid source.

• Ethnicity, Nationalism and Conflict in the South Caucasus: Nagorno-Karabakh and the Legacy of Soviet Nationalities Policy by Ohannes Geukjian (2012). A more specific look at Soviet nationality policy and it's impact on Nagorno-Karabakh, but Armenia factors in here quite a bit as well.