Dear Rosie & Sherry,

We are writing as two concerned parents. Our 36-year-old son Dan is growing increasingly frustrated about his inability to find a marriage partner. For years, we took the attitude that it was just a matter of time – that it might take a few years to find the right girl. But lately we suspect that might not be the only reason why he's having trouble.

Part of the problem stems from his seeing many of his friends get married and start families, and it hasn't happened for him. This leaves him feeling despondent.

Beyond this, our son is having trouble with dating itself. From feedback from some of the women he's dated, it sounds like he is too intense and serious on his dates. He doesn't know how to relax and enjoy the other person's company. Some of the girls he's dated feel he lacks social skills, that he can't have a normal flow of conversation.

We never thought of our son as socially awkward before. It seems the problem is getting more severe over time. He seems to be changing for the worse – becoming more unhappy, more serious, more rigid about what he wants in a wife, more quiet and introverted, and unable to admit that he needs help. Whenever we try to discuss this in a sensitive manner, he goes on the defensive.

We have other children who are married, and while things weren’t 100% smooth for them while they were dating, we never saw these kinds of issues. We can't stand by and watch our son grow more and more frustrated and unhappy. Can you offer some concrete suggestions for how to help him?

Dear Concerned Parents,

Parents like you, who try not to meddle in their adult children's lives, can be justifiably concerned when they see a child's growing frustration and unhappiness. It's difficult to know when to speak up, and how to share your observations and advice when the child hasn't asked for them. Most important, you want him to improve his situation.

Occasionally, parents and their adult child are able to have a constructive discussion about a personal issue. But as you’ve experienced, parents often have a limited impact on an adult child who does not want to receive unsolicited advice – particularly when it comes to dating. Like you’ve experienced, the child may go on the defensive and reject constructive criticism – “tuning out,” even though the parents may be offering very good suggestions.

So it appears that the two of you will not be involved in this process unless your son opens up and shares information with you.

Thankfully, however, there’s an alternative to simply standing by and watching your son's self-esteem deteriorate. You can have a third party broach the subject. Find someone that your son trusts who can approach him about his dating. This might be a married sibling or cousin, or a close, married friend who feels comfortable talking about it with him.

Once you’ve found this third party, you need to you step back. Do not become a part of this process, unless your son chooses to share information with you.

This person can begin by expressing to Dan how much he cares about him; how he knows he's been dating a long time; how he would like to help your son succeed in finding the right woman to marry; how he understands that many people who’ve been dating for a long time get frustrated and upset, and even feel burned out; and how he’s concerned this may be happening to Dan.

Unless he makes some changes, his frustration will likely increase.

He can also explain that if your son he keeps dating the way he's done in the past, without examining to see if he would benefit from some changes, his frustration will likely increase. Dan might begin to reflect these negative feelings when he interacts with dating partners, hurting his chances for any promising match to succeed.

This first conversation is not the time to bring up any of the observations you made in your letter to us. "Constructive criticism" won't serve any purpose at this point in time and may be counterproductive because it will put your son on the defensive. The only goals of the conversation are to let him know he is loved, that he's a good person who deserves to find the right partner in life, and to get him to think about using a mentor, who can be either that friend or someone else Dan chooses.

The mentor should try to "normalize" what your son is going through. Many people have to date a long time before finding the right person, even though they are very well put together in the other aspects of their lives. A mentor isn't just a "cheerleader." The mentor should work with your son to discover what changes he should make in how he goes about finding women to date, the criteria he uses to accept a suggestion, and his actual dating style.

In time, we hope that your son will be able to identify some unproductive patterns (as well as positive aspects of his dating), and figure out what changes need to be made to turn things around.

Easing the Tension

We can also offer some concrete advice for Dan and his mentor about a difficulty you already know your son has – he is so tense on a date that he can’t have a conversation that flows and enables each person to learn a little about the other. Here are some pointers that have helped many people feel more comfortable on their dates:

  1. Be selective about whom you date. Say yes to people who sound as though they share your values, want similar things out of life, and have some of the character traits you’re looking for. Don’t agree to go out with someone who doesn’t sound suitable simply because someone pressures you or because you think you must accept any offer that comes your way. Simply knowing that you and your date share some common ground can help lower your anxiety about having something to talk about or relate to.
     
  2. Be well-rested for a date. If you’re tired, you may find it hard to concentrate on the conversation, and if you haven’t given yourself time to unwind after a busy day at work, you’ll bring that tension with you on the date, and it will only exacerbate the nervousness you feel about dating.
     
  3. Lower your expectations. A wise woman once told us, “Don’t expect, and you won’t be disappointed.” Too many of us put so much hope into those first few dates with someone new, fantasizing that “we’ll hit it off right away” or “we’ll just know it’s right for us.” Both of these expectations are unrealistic; it often takes a few dates before two people begin to connect and realize they may be good for each other. Simply tell yourself, “I’m going to meet a new person, to learn a little about her.”
     
  4. If you have trouble with the flow of conversation, strengthen your conversational skills. List a number of topics that are good to talk about on a first, second, or third date (see Dating Maze #164 for suggestions). Then, list some interesting points you can raise about each of them, as well as questions you could ask your dating partner, and review this list a few times. It may also be helpful to role-play a few dating conversations with your mentor, or with a friend or family member.
     
  5. Greet your date with a smile. You’d be surprised how quickly a smile can lower the level of tension between two strangers. And try smiling from time to time during the date – when you describe something you enjoy doing or when your date says something complementary, interesting or funny.
     
  6. Don’t let the date last too long. Two to three hours is plenty for a first date. And if you can’t imagine conversing that entire time, incorporate an enjoyable activity into the date. One man we know learned that his date liked board games, so he planned a first date at a café where they played backgammon, interspersed with coffee and conversation.
     
  7. Don’t arrange for more than one “first date” at a time. Give yourself a chance to see if you’d like to go on a second and third date before planning to meet another person. And try to take breaks of a few days between dating partners.
     
  8. Enjoy the rest of your life – don’t put things on hold because you hope to meet your life partner. Find a regular exercise program, take that course you’re interested in, plan that vacation with your friend. When you have joy and meaning in your everyday life, you’ll project those positive feelings to your dating partners and will feel less tension yourself.

In closing, we reiterate that your role as concerned parents is to be supportive in every way, and to find a third party who can broach the subject of a dating mentor. Most of the people who have used mentors say this help was invaluable. We hope that your son experiences the same, and is soon back on a productive dating track.

Rosie & Sherry