Dating Maze #290 - String of Disappointments


At age 31, how can she “catch up” to her peers in the dating process?

Dear Rosie & Sherry,

I am 31 years old, smart, friendly and pretty, though a bit introverted and slow-to-warm-up at times. I have many close friends, though I have never had a boyfriend. This concerns me because I really do want to be married and have children. School and work have kept me busy for a very long time and I have very little dating experience. My parents were very education-focused and dating was not encouraged growing up -- though ironically, “marry a Jewish guy” was frequently mentioned.

When I go to social mixers, I feel like a fish out of water. It's like I'm a visitor in a foreign land and ignorant of the local customs. Also, either at mixers or online, I don't see many guys who interest me. I've tried to “just give him a chance” as friends advise, but even when I do make a concerted effort to keep an open mind, usually we just don't click. I imagine this is par for the course, yet I seem more sensitive to it and am saddened by the rejection -- even if little time has been invested (i.e., one date) and even if I’m the one who decides it's not a match.

I feel like a sensitive teenager in adult shoes.

My senior year in college I did meet a wonderful Jewish man, but after a few dates nothing came of it. So I am encouraged by the fact that I found someone I really liked. (Yet this has happened only once.) Yet even if I were to find someone great to date, everyone says that “first love never lasts.” So I envision a never-ending string of dating disappointments, having to start all over again in a no-win situation.

I want to share my life with someone and create a loving Jewish home. I feel I have a long way to go between where I'm at now and the goal I wish to reach: it is overwhelming, especially since this dating stuff is not easy for me. I feel like a sensitive teenager in adult shoes, a real-life “13 going on 31.” Where do I start? How can I catch up to my peers and enjoy the process? What can I do to help myself reach my goals without feeling so pressured? Thank you for any help and advice.


Dear Anita,

We appreciate how difficult it was for you to write to us, and we're glad to have the opportunity to address this big challenge in your life. Although you may feel as though you're the only 31-year-old who is just beginning to date for marriage, we can assure you this is not true. We've heard from many other women and men who are in the same position, either because they delayed serious dating until they finished schooling and embarked upon their careers, or because they finally decided to look toward "settling down" after years of short-term, not-serious relationships. In spite of the many different reasons for a late-start, each person in this situation is embarking on a new, unfamiliar process in their journey through life.

Fortunately for you, that levels the playing field for someone who hasn't gone on many dates, and someone who is more experienced but dated solely for entertainment or companionship. Both of you now need to develop beneficial criteria to choose a dating partner, and also reasonable expectations for a “first date.” You’ll need an understanding of the different ways that attraction and connectivity can take root and grow, and the tools for deciding whether to continue with a courtship and when to make a decision about engagement or marriage.

It’s an advantage to not have a long history of casual dating.

In one respect, someone like yourself, who doesn't have a long history of casual dating, has an advantage over her friend who claims, "I've been dating so long I'm a real expert." You're more receptive to suggestions about productive dating and you don't have to unlearn some unproductive patterns from the past. Essentially, you'll be starting from a fresh perspective and incorporating a way of presenting yourself and evaluating dating partners that is likely to enable you to build a relationship that will lead toward marriage.

How do you go about that? Reading the archives of this column is a good first step, as well as articles on our website, The pointers they contain will help you become more attuned to where you are going in life and the type of person you're looking for. You’ll also learn about networking and using other resources to find dating partners, how to develop reasonable expectations regarding dating and marriage, and guide you through the process of building an enduring relationship. We also recommend that you find a married person you trust who can be your dating mentor, to be your sounding board and offer useful guidance while you are dating.

Good on Paper

You write that because of your inexperience, you're worried it will take you a while to become "good at dating," and that your opportunities to get married soon will be further delayed because the first few people you date will be sort of like "test runs." When it comes to dating for marriage, that's simply not true. On the date itself, you should be genuine, and not worry about being “sophisticated enough.” You’ll need decent conversational skills -- knowing how to express interest in another person and how to share basic information about yourself. If this is hard for you, try to role play a couple of dates with a friend in order to increase your comfort level and improve your conversational skills.

What comes before a date is also extremely important to its likelihood of success. You should only be dating men who are close to what you are looking for. We suggest that before saying "yes" to a dating suggestion, you find out enough details to get a sense that he is "in the ballpark":

  • you're comfortable with his biographical details and background
  • he has similar goals and values as you do
  • he has some personal qualities that are important to you
  • he'd like to meet someone like you, for the purpose of marriage

If you start from this point, you'll save yourself a lot of wasted time discovering that you and your new date have too little in common to warrant investing your energies. If he at least seems good "on paper," you'll have something to build upon if the two of you sense your personalities might be compatible. And believe it or not, sometimes one of the first people you date in this manner ends up being the Right One.

Networking Tips

We'd like to address your comment that you feel uncomfortable at social events like mixers and worry that this is going to keep you from meeting many potential dating partners. First of all, remember that you only need to meet the man you're going to marry -- and you don't have to be a social butterfly at a mixer to do this. In fact, most people we know are not social butterflies and feel very uncomfortable at mixers, particularly ones with a lot of people, which often make them feel anonymous at the event and badly about themselves after they return home.

We prefer smaller social events like a Shabbat dinner, a game night organized by a friend, or a small get-together that features an activity that facilitates interaction and conversation among the guests. People feel more comfortable at events like these, find themselves connecting to more people than they ever would at a large mixer, and often decide to date someone they've met, or to try to set one of the other guests with a friend.

Introductions by friends is a best way to meet dating partners.

Introductions by friends continue to be one of the best ways to meet potential dating partners. In this regard, it's important for you to develop friendships within the Jewish community. We suggest that you consider joining a synagogue, signing up for a Jewish adult education class, attending exercise classes at the local Jewish community center (as opposed to a commercial gym), and participating in a Jewish community project. You'll meet and become friendly with Jewish people of all ages, and hopefully some of these new people in your social circle will have good ideas about setting you up.

We suggest going this route for a while before exploring the possibility of finding potential dating partners on Internet sites. We know many married couples who "met" through dating websites, but the Internet is not something we recommend to people who don't have a lot of dating experience. If at some point in the future, you decide to look into Jewish dating sites, we suggest that you first read our article, “Maximizing Dating,” so that you can use this resource effectively and avoid common pitfalls.

In closing, we'd like to make an observation about your college "romance." You tell us that the fact that you really connected to and cared about a Jewish man had a positive impact on how you see yourself and your ability to connect to someone in the future. This is exactly the perspective we would want you to have. You and this man were probably both not ready for something more enduring, but you did learn a lot about relating very deeply to another person. If you allow yourself to grow from this early, positive experience, you'll reap many benefits when the right person comes into your life.

We wish you success in navigating the dating maze,

Rosie & Sherry

Next Steps