He's in his 30s or older, You're in your 20s

Chances of it Working

Excellent: An older guy tends to offer more stability and commitment than a 20-something one does.

How to Beat the Odds

Obviously, guys in their 20s do settle down (take Ashton Kutcher and Maria Carey's man, Nick Cannon, for example) - it may just take him a while to get comfortable with monogamy and not feel rushed into things. If you're game to play it patiently, you'll probably appreciate his sense of fun, his sense of adventure, his energy (especially in the sack) and how unjaded he is.

Mismatch

He's in his 20s, You're in your 30s

Chances of it Working

Poor: Most young men aren't into serious relationships yet. And whereas you may be thinking of starting a family, he probably isn't.

Mismatch

He has money, You're on a budget

Chances of it Working

Good: Men love showing affection by treating you to things you otherwise wouldn't have access to, so being able to do that will strengthen your bond.

Mismatch

You have money, he's on a budget

Chances of it Working

Poor: Men are still raised to believe that they need to be financially successful, so he'll probably feel that he doesn't measure up.

How to Beat the Odds

Play up his talents, whether it's his encyclopedic knowledge of current events or his amazing ability to work magic with absolutely anything electronic. Then rely on his skills by asking him for help in those specific areas. When you let him prove how useful he is, he'll internalize that you need him and see himself as a strong partner.

Mismatch

He's introverted, You're extroverted

Chances of it Working

So-So: You'll want to share your social life. He may go along at first to please you, but once he pulls back, you could feel frustrated.

How to Beat the Odds

Save your social-butterfly tendencies with your friends and bring him only to the most important events. And when he does come out, don't ditch him for the dance floor - make a point of introducing him to people and emphasize what they have in common, since introverts feel comfortable only when they're making a one-on-one connection.

Mismatch

He's extroverted, You're introverted

Chances of it Working

Poor: Social interaction provides fulfillment and status, so he’ll expect you to hang in his world without getting clingy, quiet or pouty.

How to Beat the Odds

Making the effort to RSVP 'yes' to things will show that he matters to you. Just ask him to prep you on people's basics (their jobs, hobbies, passions, whatever) ahead of time. You'll feel better steeled to make small talk (even if you don't join the conga line). And suggest easy double dates with those of his pals you know you like. Mismatch

He's laid back, You're structured

Chances of it Working

Good: Though it may cause friction now and then, his laissez-faire attitude is probably part of what attracted you to him, and he'll help you loosen up.

Mismatch

You're laid back, His structured

Chances of it Working

Good: Having someone whose so on top of things makes a woman feel secure. Plus, you'll both enjoy breaking him out of his routine.

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