He prayed istakhaarah and did not feel anything

The daleel (evidence) for Salaat al-Istikhaarah and the duaa
to be recited is the report narrated by al-Bukhaari (1109) and others from Jaabir
ibn Abd-Allaah (may Allaah be pleased with them both). For the commentary
on this hadeeth and more details, please see question #2217
and 410.

With regard to what some people say, then he should go
ahead with whatever he feels happy with, a hadeeth to this effect was
narrated from the Prophet (peace and blessings
of Allaah be upon him) narrated by Ibn al-Sunni according to which
he said, If you are concerned about a matter, then make istikhaarah seven
times, praying to your Lord, then see what you feel most drawn towards, and
the good will be in that.

Al-Nawawi said: its isnaad is ghareeb, and it
includes narrators whom I do not know. (al-Adhkaar, p. 132).

Al-Haafiz ibn Hajar said: if this were proven,
it could be taken as evidence, but its isnaad is very weak (waahin jiddan).
(al-Fath, 11/223)

Al-Haafiz al-Iraaqi said: it contains a narrator who
is known to be daeef jiddan (very weak), namely Ibraaheem ibn al-Baraa..
Therefore the hadeeth is daeef jiddan. (al-Futoohaat al-Rabbaaniyyah,
3/357)

The correct view is that when Allaah makes something easy for
you after having decreed it and accepted your duaa
this is a sign that it is good to go ahead and do it. The existence of obstacles
and difficulties is an indication that Allaah is pushing His slave away from
doing it. This meaning will be very clear when one ponders the meaning of the
hadeeth of Jaabir concerning al-istikhaarah, where the Prophet
(peace and blessings of Allaah be upon him) said:

O Allaah, if You know this affair [and
here he should mention it] is good for me in relation to my religion,
my life, and end, then decree and facilitate it for me, and bless me with it,
and if You know this affair to be ill for me towards my religion, my life, and
end, then remove it from me and remove me from it, and decree for me what is
good wherever it be and make me satisfied with such.

Ibn Allaan after transmitting the scholarly view
that the hadeeth of Anas is daeef (weak) said: Therefore it was
said: that after (doing istikhaarah) he should do what he wants (i.e., even
if he does not feel that sense of being happy), because whatever happens after
doing istikhaarah is good

Al-Haafiz ibn Hajar said: Al-Haafiz Zayn al-Deen
al-Iraaqi said (concerning doing something after praying istikhaarah):
Whatever he does, there will be good in it. This is supported by what is said
at the end of the hadeeth of Ibn Masood according to some of its isnaads:
Then let him make his decision. I (Ibn Hajar) say: I have already
discussed above and explained that its narrators (i.e., the narrators who added
the phrase Then let him make his decision) are daeef (weak). But
this is still stronger than the narrator of that hadeeth (i.e., the hadeeth
which says, then see what you feel most drawn towards). (al-Futoohaat
al-Rabaaniyyah, 3/355-357)

Another of the myths that are widespread among people is that
after praying istikhaarah you should sleep, and whatever good you see in your
dream that makes you happy means that what you want to do is good and will be
made easy for you, otherwise it is not good. (This is what the questioner meant
by saying gets the message). There is no saheeh daleel (evidence)
for this as far as we know.

The above does not mean that if you feel happy it is not a
sign, but this should not be regarded as the only sign about whether or not
the matter is good. People often make istikhaarah about something they like
or want to do, so they feel happy about it from the outset.

Shaykh al-Islam [Ibn Taymiyah] (may Allaah have
mercy on him) said concerning the matter of feeling happy about something: if
he makes istakhaarah, then whatever Allaah makes him feel happy about and makes
easy for him, this is what Allaah has chosen for him. (Majmoo
al-Fataawaa, 10/539).

There is a difference between making feeling happy the only
sign and making it one of several signs. There is no set time period for salaat
al-istikhaarah; it is permissible to repeat it more than once, but there is
no limit to how many times. The person may offer the duaa before
or after saying the salaam. And Allaah knows best.