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Dating at middle age is more mature, less pressured, less hormone driven, less at stake, less to prove, more relaxed. There’s the 20/50 Rule (I just made it up). For a 20yo, “the rest of your life” means 50+ years (plus the travails of raising kids) but, for a 50yo, it means 20+ years (and enjoying the grandkids). But expect both people to be more set in their ways — meaning, expect mismatches (and the accompanying disappointment) over seemingly small issues. Don’t take it personally. Meeting parents and family should carry fewer connotations. Family gatherings should be less stressful. At middle age compared to young adulthood, you’d be surprised how you naturally have much more in common with your SO’s parents (see health issues below). You are a better-known quantity, and there should be less of a critical eye on you due to the 20/50 Rule. Beware of middle-aged crises in both parties. Compared to younger days, expect a longer “courtship” to discern someone’s nature for a variety of reasons (crisis being just one of them). I’m a sensitive guy, but I’m still surprised how much middle-aged (and older) women talk casually about their personal health issues on dates. I think it’s expecting a lot for a guy to listen to tales about fibroid tumors, pap smears, mammograms, lumpectomies, etc without getting the heebee jeebees. This is definitely not a cure for loneliness. See a doctor. I don’t know what was meant by “diving in head first”. There’s a lot more nasty diseases creeping around out there (and people don’t even feel sick!), compared to getting the clap or the crabs 30 years ago (where one knew rather quickly). Some stuff (herpes, HIV, etc) never goes away. Be yourself, trust your intuition. There are fewer “fish in the sea” now, but they are of a better-known and proven quality. The field is naturally much broader, distances can be much greater. More individualism, less social pressure, less running with the crowd, generally less of a social setting. This means less social talk (honest info or gossip) to affect one’s opportunities with the next person. But it also makes it easier for someone to have another ongoing (or recurring) love interest somewhere else. The Internet helps foster this as well. Women seem more susceptible than men to feeling lonely and incomplete. Beware of your recovery process from your previous marriage, whether it ended by divorce or death. Don’t buckle to anyone’s pressure (mom, sis, kids, him, etc) to be “fulfilled again”. People will also have different “baggage” at this point in their lives, and they might manage it differently. Some people barrage their dates; other meter it out appropriately, while others hold back. Compared to younger years, expect baggage to involve more health issues, career changes, end-of-life issues for parents/siblings/self, retirement funds, portfolios, fixed income, retirement options (stay here or retire elsewhere). IT has become part of a people’s personality. Be aware of the time and subject matter spent on phones/TV/computers. IT steals the other person away from you, even when you supposedly watch TV “together”. Speaking on the phone while ignoring someone in the flesh has always been disrespectful; that’s why people apologize for doing it. Don’t worry about kids and grandkids driving someone away.