Here are a few of the most important factors to consider when entering into a relationship with someone considerably older (or younger) than oneself.
1) Finding Common Relationship Ground
One of the most important factors to consider when entering a relationship is what commonalities are shared by the two people involved. That's not to say that both people have to enjoy all of the same things; that would be boring, but enough shared interests/hobbies are important...
Compromise will ease the strain and the difference in personalities can help both people involved to better themselves. An older partner's maturity can help a younger partner become more mature, while a younger partner can allow an older partner to relax a little and be reminded of what it's like to be less responsible.
2) Making More than Just a Physical Connection
Just as important, maybe more so than common interests, is a connection that extends beyond the physical. Just because a partner is physically appealing now does not necessarily mean he still will be ten, fifteen or twenty years later.
Making sure there is an emotional connection will be the key. Both partners will have to deal with the questions and possible outright objection from family and friends because of the decision to be with someone who is significantly older/younger. Knowing that a partner is there for support will make the relationship stronger and help both people grow not only in the relationship, but also outside of it.
3) Sharing Long-Term Wants and Goals
Being on the same life path is often a major obstacle for age-gap relationships. A man in his mid-30s may be preparing to get married, start a family, etc., while a woman in her early-20s is just figuring out what she wants in her life. She may want a family, eventually, but not in the same time-frame as her partner.
Keeping the lines of communication open and being completely honest with each other will allow the age-gap couple to figure out their projected lives, whether together or separately.
4) What Level of Maturity is Held
While considering all of the above mentioned criteria, another important aspect to keep in mind when considering an age-gap relationship is the maturity of the people involved. It's a common preconception that men mature more slowly than women, hence the prevalence of older man-younger woman age-gap couples. With this rise of the "cougar" (older woman-younger man relationship), the question of maturity comes into call more so than ever...
In the end, when it comes to relationships, all that matters is the connection between the two people; age is just a number.
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