Things to keep in mind when choosing games:
1. Skill level:
Often puzzles will have a star rating or some indication of the difficulty of the puzzle or game. Brain teasers and mind benders often have ratings on them, and you'll want to check that before you purchase. If the recipient has not done many of that sort of puzzle before, better off starting them on an easier level. However, they don't necessarily have to be experts at puzzles to do the hardest level - they may be naturally brilliant and have the smarts to start off with a challenging one right away!
2. Age of individual:
This criteria for choosing a game is rather self-explanatory and is similar to skill level. Make sure the game is age-appropriate. If it's too kid-like for a teen he will be very unlikely to play such an "uncool" game; however, conversely, if you give him a game or puzzle that is beyond his reach due to his age, he will likely give up on it and may even be hesitant to revisit it when he is older.
3. Number of players
Are you wanting to buy a family gift, or something the teenager can occupy himself with, or a game suitable for a party? Jigsaw puzzles are a great family gift. I have wonderful memories of my family getting together with a few friends on Christmas day and putting together jigsaw puzzles while enjoying the Christmas goodies and drinks. Jigsaws are ideal for small groups of all ages and are a great pastime, as you can be engrossed in the activity while still enjoying stimulating conversation. The majority of board games are also designed for small groups and would make a wonderful family gift.
There are so many games out there for individuals. For gifts for him, you don't have to just settle on a deck of cards to occupy himself with solitaire anymore! There are many coffee table puzzles or mind challenge puzzles on the market designed specifically for individuals. These often come with a suggested time you can do it in, giving you a challenge to race against the clock. These mind puzzles make particularly appropriate gifts for him, for those who like a challenge and are systematic by nature. As mentioned above, there are various skill levels, so check the puzzle before you purchase it to make sure it will be the perfect gift for your recipient.
While board games and puzzles make excellent family gifts or gifts for him, for parties or a games' night you'll generally need something a bit more versatile that can easily be expanded or shrunk for your sized group. Taboo, Scattegories, Charades, and Pictionary are all popular party games, and some of them you can play using just a dictionary or your creativity, to save you purchasing the official game (shh...nobody heard me say that!).
4. Size and number of pieces:
Larger puzzle pieces, and less of them, will be much more appropriate for a younger audience. Giving achievable goals, in the form of puzzles, will stimulate a child's creativity and engage them in what they are doing without leaving them frustrated to tears because of the unattainable challenge placed before them. What was meant to be a fun present can easily turn into a nightmare if the puzzle is too big or the instructions to a game are just too confusing. If you do want to give an otherwise complicated puzzle or game to a younger audience, consider having an older child or adult work alongside the recipient, helping him/her understand the rules (showing is often far superior to explaining), or helping them tackle bite size segments of a puzzle.
5. Speed of game:
I for one do not like slow-paced games. I love action games and puzzles, such as speed Scrabble (regular Scrabble is too slow) and Dutch Blitz. If you were to give me one of those tricky mind challenge puzzles, I would be bored and frustrated within a few minutes. However, give the same game to someone who likes a challenge, is methodical, and loves to systematically solve problems, and you will have found the perfect gifts for him! Generally personality or even profession is a good indicator of what style of games the individual might like. Is he a people-person and loves activity, or does he have a more subdued personality, enjoying pondering puzzles and thinking through the challenge himself?
In a nutshell, if you take into consideration the things you know about your recipient, you should be able to find games and puzzles to make perfect gifts for him, gifts for the family, and party games. Have fun, and happy puzzling!