That's a very good question! There is so much stereotyping associated with the Death card. Particularly that of "an ending or negatively aspected". The true meaning of the Death card is transformation. It is a process in which we all much go through in order to grow and evolve upon our own path of understanding and self discovery.
Life is a Great Wheel that turns around and around in a circular motions as we go through the seasons, years, cycles and phases of our life. As with each season, cycle and phase there are many lessons that we each must learn before we can move forward onto the next spoke or turn of the wheel.
Only through transformation can we become more in alignment with our true purpose, self and dreams. But one cannot transform oneself without first releasing the things within that do not reflect who you are in this moment. Outdated emotions, beliefs, thoughts, judgments, inner debris that no longer serves the same purpose as they once did.
By releasing these things, we open ourselves up to receiving more positive opportunities, people and things into our lives. The old saying "A cup that is full has no more room" is exactly the very thing I am talking about. If we are filled up inside with outdated emotions, negative thinking patterns, issues that we have not dealt with, etc. all of these things must be released before there is room for the good things to manifest more easily into our life. It's hit and miss when there's so much inner debris so the Death card signals a time in which you will be releasing a lot of things that no longer serve your higher purpose to help you move forward and achieve your goals.
It is a period of redefining yourself and who you are and clarify what exactly you want in your life. When one door closes, another one opens. This too is important because it provides hope of better opportunities that will come knocking on the door in the near future.
This card could easily signify that in order for a reconciliation to occur with a past lover there must be a willingness to change habits of the past that were problematic in order for there to be growth in the future. If there is not willingness for both parties to release the past in order for you to step forward into the future together then it will not be very fruitful and further impede your progress.
In that instance, it could signify that you need to be clear of what your expectations are and what his expectations are clearly before jumping into the fire before checking to see how hot it is first. As you know sometimes the past can bring back painful memories, old emotions, old thoughts, judgments, etc. so this should also be implemented within the interpretation of the Death card.
The Lover's card is more than a unity card; it also signifies the complexities of relationships and the many challenges that we may encounter with our relationship to others and ourself. This card also signifies that we need to be realistic about what we want in a relationship and in a person. Often times we nitpick our mates to death trying to get them to be more in the likeness of what we expect them to be that we miss the opportunity to embrace the love that is available but through incessant harping may hinder the other person's feelings making it difficult for them to truly connect with us for fear of not meeting our expectations.
So it is important that we make wise choices in our selection those we have relationships with so that they are more in alignment with our needs from the get go not after we "mold" them into what we expect them to be. As we know truly we cannot change anyone other than ourselves and how we react to situations. So the Lover's card asks us to evaluate our relationship with others and ourself. If we do not love ourselves and appreciate/value our own individuality/uniqueness then how can we truly expect others to? This is what the Lover's card signifies. A look into the relationship you have with yourself in comparison to those around you. If there is self doubt or low self confidence or a lack of willingness to look within oneself to find the root cause of a problem will result usually in this card being reversed.
The Nine of Cups would represent fulfillment and happiness through having overcoming the challenges presented by the situation as a whole. It signifies a completion and emotional gratification, a cup that is full this time of abundant blessings where as before it was filled with chaos, confusion, fear, anxiety, confusion, worry and inner debris. Through going through the process of transformation we redefine ourselves and our life and in the process find that we will attract individuals who better match our true needs and are very compatible with us and aspire us to reach our goals and dreams.
I will say that from my own feeling, the past relationship will only work if he himself has gone through a process of transformation and has released his attachment to the past and willing to embrace the future with an open mind. On the other side of the coin, this configuration of cards together can signify that once you are more balanced and clear within yourself who you are and what you want then the relationship and happiness you are seeking will manifest itself once you've reached a certain part of the process but first you must go within and discern what must be released and has sabotaged your efforts in the past. The Nine of Cups signifies that through this process for about 9 months you will go through a transformation and upon it's completion you will be much happier and more in alignment with the person who will best match your needs.
Hope this has been helpful and many blessings upon your path!