Dear Rosie & Sherry,

I am 39 and I really want to get married and have my own family. I'm intelligent, looking to grow and learn, and consider myself a good person. I receive a number of suggestions about dates, but I have a problem in that I rarely connect with people. I am shy and quiet, and while I will spend time chilling with a friend, I soon need to retreat to my own space again. I've had a hard time connecting to the men I've dated.

I recently I met a man through work whom I really like. He is intelligent and sweet, and we seem to speak the same language, both philosophically and analytically. However, there are two problems. He is more than 10 years younger that I. Also when it comes to spiritual issues – particularly Jewish observance – although he says he understands it philosophically, intuitively his heart has trouble connecting.

I’m confused about whether or not I should be dating a man who is religiously observant because I’m still discovering how I want to incorporate Jewish observance into my life. No one in my family is religious, so I don’t have any models to follow. And even though I've spent a number of years trying to discover the spiritual direction I'd like my life to take, I am still internalizing the meaning and significance of many of the practices I've chosen to follow.

So on one hand, I'm concerned about dating a man who isn't observant, only to discover a few months down the line that we have a problem. On the other hand, it seems more simple to date a man who is not observant. So I'm not sure what to do. Can you help?

Anita

Dear Anita,

Thank you for writing to us. You are describing a fairly a common experience for someone who is in the early stages of becoming more Jewishly observant.

Even though you want to get married and feel this is a critical time for pursuing that goal, it's scary to imagine settling down with someone when you can't be sure that your lifestyles coincide. And while you feel more comfortable dating someone who isn't as religiously committed as you are, you wonder whether you'll have a conflict about religious observance if your relationship becomes more serious. We understand these concerns.

The answer to resolving your dilemma is that you need to acquire more clarity about where you are currently holding in terms of your Jewish observance, and the direction in which you'd like to grow over the next few years. It's not easy to attain this clarity on your own, because each time you modify an aspect of your religious commitment, there's new information to learn, questions to be answered, and perspectives to understand and internalize. From the tone of your letter, we surmise that you're doing a lot of this process on your own and don't have a strong educational or support system. And it's a lot to process by yourself.

Find a mentor who can give you a model to emulate.

Most people find that having a mentor can provide much-needed support, guidance, and understanding to help feel more grounded and focused. Our advice to you is to find a rabbi or Jewish educator who is familiar with outreach work and can give you guidance and a model to emulate. They'll be able to help you pace yourself so you don't rush into new things too fast and later feel overwhelmed.

Another crucial element for people who are becoming more observant is one or two surrogate families who can host you for Shabbat every few weeks and for Jewish holidays. This is how you see Judaism in practice – how a family makes Shabbat special, how the husband and wife interact with each other and with their children, the way they keep their home kosher, their involvement with the Jewish community, and how they incorporate Torah values while busily supporting a family, running a home, and raising children.

Gradually, you can begin to visualize the way you want your own life and home to be, and this clarity will form the basis of your search for a life partner.

We often remind out readers that common values and compatible goals are the cornerstones of enduring relationships. If a couple doesn't have this common ground, they are likely to find themselves in an ongoing struggle about what each wants from the marriage. Once you are on firmer ground yourself, you can decide if you can be comfortable with someone whose level of Jewish observance is different than yours and add this consideration to the other personal qualities you are looking for in a potential marriage partner.

Sense of Connection

We'd like to bring up a delicate point at this juncture, an "elephant in the room" that we'd been remiss if we didn't address. Because you're 39 and want to get married and have a family, there is a sense of urgency. This means that you don't have the luxury of taking several years to find the clarity we've spoken about.

Which brings us to the subject of the man you met through work, who is 10 years younger than you. We have a few concerns about whether the two of you have enough common ground to begin dating and developing a lasting relationship. You feel that the two of you can relate on different levels. However, there are some basic issues that you need to address. First, is each of you comfortable with your age difference? If may not be a big concern if you are dating and just getting to know each other, but it may play a major role in your decisions about marriage, and you need to be honest with each other when you talk about this.

Beyond this, you want to get married and start a family, but does he? Many men in their late 20's don't feel that they're at that stage in life. Have you spoken with him about your respective timetables for marriage? If you're dating for marriage and he isn't, from our point of view you shouldn't even consider dating him.

In addition, how much do you know about each other's life goals and values, other than his belief that philosophically he understands the value of Jewish observance?

Think about how you felt when your friendship began.

You mention that you have had a difficult time connected with most of the men you’ve dated. Even though this man from work might not be the right person for you to date, there is something very positive in the fact that you feel comfortable with him and a sense of connection. It means that you actually can connect to with a man other than one of your close friends. And even though he may not be right for you, it's very likely that there are other men who are more suitable for you, whom you can also connect to.

People who are shy and introverted often have trouble relating to someone they don't know well and opening up to them. The pressure of being on a date often makes it even harder for someone who is reserved to start to connect to another person. You may have been more relaxed with this person because you didn't initially think of him as dating material, and your conversations evolved from being work-related to more personal. We'd like you to think about how you felt when your friendship began – you may be able to recall this experience to help you when you are on a date with someone new.

In addition, we'd suggest that you find a good friend or a coach (who specializes in helping shy people) to help you learn and practice conversation techniques that can help you feel more comfortable when you are with someone you don't know well. Many people who describe themselves as shy or introverted feel they will never be able to form a connection with a date. This simply isn't true. They can connect, and the fact that they have a few close friends proves this. They simply have to strengthen their style of communicating and adapt it to dating so that they can gradually be more open with their dating partner and form a connection. Our recent Aish.com article about “Dating for Introverts” offers some suggestions you might find helpful.

We wish you success in navigating the dating maze.

Rosie & Sherry