Why marry? The mystics explain that the natural compulsion to marry expresses a deep soul-ambition: its desire to reconnect with its other half. Every body is occupied by half a soul. Body and soul reach completion when they are reunited with their other half.
And it's a mitzvah. In fact, a Jewish home is one of our greatest mitzvot So we don't just wait for Mr./Ms. Right to appear—we actively search them out.
The mitzvah starts, and the search commences, at age eighteen. Don't worry about a perceived lack of financial ability. G‑d who sustains all of creation can and will provide for one more family!
Whom to Marry
Obviously the person you will marry should be compatible with your personality and particular emotional needs. But here's the Jewish angle:
A Jewish marriage is also a commitment to the continuity of our nation. Jewish parents raising Jewish children with Jewish values is our non-violent way of combating all the bigots who aspired to relegate our people to the annals of history.
There are also certain technical matters to be taken into consideration. Among them: certain restrictions on whom a Kohain can marry, and ensuring that your potential spouse has received a valid get (Jewish divorce) if previously married.
Dating
In Jewish tradition, dating is not intended for entertainment purposes; it is reserved for men and women actively seeking their life mate.
Jewish law precludes a man and woman from being secluded together. Thus, the preferred venue for a date is a public or semi-private location.
Successful dating requires the mind to exercise its judgment in an area which instinctively belongs to the heart. Obviously, the heart, too, must be involved. But the mind blindly following the heart can be a recipe for disaster. Allow yourself to "fall in love," but only after your mind has decided that this could be the right person for you.
For more on this topic, see our section on Finding Your Soulmate.

i met my wife a very unusual way. I was 26 and had been shidduched with a girl (not my wife). We agreed to meet at a kosher restaurant in my area. I was waiting for about forty-five minutes, and she didn't show. I checked my phone and saw that she had blocked my number.
Across a table from me, I saw a young Jewish woman. She smiled at me and I asked if she was waiting for someone. She said she was going on a first date from a shidduch and the man hadn't shown. We ended up having dinner and arranged a second date. Now she is my wife and we have four children. It really was b'shet.
what a cute and adorable story. it makes me hope and feel inspired that even at the age of 42, i can still find love. just gonna go hang out in kosher restaurants in the hope of finding the one. this is a true example that Hashem always provides
Not everyone is the same though
Hi Rachel, my son's friend is a wonderful 53 year old man, would you be interested?
Doesn’t god prepare for every man and isn’t marriage a biblical commandment?