Advice: Dating an Older Woman

I am a never-married male, 29, dating a woman of 45 who has two kids from two previous marriages. We've been seeing each other for over a year in secret. My family hates the relationship. Only recently have I been open about it with my brother, who is no fan of it, either. My mom threatens to never see me again and to cut me out of her will. My family believes this woman is out to get me, and that I don't need someone twice-married and 16 years older. I tell them we get along well and I enjoy her kids very much. I've always been close to my family. My parents won't even meet her. What's the best solution?

Having twice failed at marriage is far more serious than the age issue. You need to make sure that a long-term relationship could stand on solid ground. Which means you have lots of information-gathering to do. You should be talking to your girlfriend about her past. Why did each marriage sour? If she's blaming her exes, view it as a danger sign; it means you'll be the next target. If she has no insight into her own contribution to failure, or refuses to talk about her past, then get out now. And by the way, how long did she wait between ending each marriage and starting a new relationship? Rushing into a new relationship leaves no time for reflection about what went wrong , or time to reset the psyche. The odds of a successful remarriage (or cohabitation) on her part are not great, made all the worse by the presence of two children. This is not a commentary on their characters or likability, but an acknowledgement of the fact that pre-existing children vastly complicate new marriages, often around issues of money and discipline. What your family may worry about is that your girlfriend needs a partner to make her life easier and that need supersedes interest in you as an individual. It's a legitimate concern. There's the extra income. But more, raising kids as a single mom is difficult, no matter how glamorized it is on television. Enjoying a girlfriend's kids in the absence of obligations is one thing; attitudes and expectations invariably change after living together. What roles do the children's fathers play in their lives? If none, why not? What responsibilities will you have toward the children? These need to be clearly defined in advance. And if you live together, would you be comfortable with the comings and goings of two noncustodial fathers—over which you'd have little control—and their significant roles in your family life? These are not very romantic questions, but they tend to overwhelm stepfamilies. There's little reason to doubt that you love this woman, but you need to know that secrecy drives much of the passion in such situations. It's hard to recognize such forces when you are being being whipped around by them. And finally there is the age issue. Yes, it makes everyone queasy because your girlfriend is probably closer in age to your parents than to you. But her age is proxy for a concern—however poorly expressed by others—that your lack of relationship experience may make you vulnerable to manipulation by a far more experienced player. They suspect that the situation presents far more advantages to your girlfriend than to you. The fact is that relationships are difficult, remarriages even more so, and a relationship that more evenly balances rewards is a minimum requirement. Stop focusing on your family's opposition. Start examining the realities for yourself.