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Advice for Older Single Guys

Advice for Older Single Guys

Eight dating tips from a guy who's been there.


Until recently, I was one of those “older single guys.” Past 35 and still not married, people always said, “We have to get you married” or “You're such a great catch, why aren’t you married”. Of course, someone always had a suggestion of a great woman. I was happy people still thought of me but it was actually pretty tiresome and exhausting. Despite the optimism and encouragement of others, I started to lose hope. Scores of dates over the years had worn me out. Too many times I’d either wasted my time or gotten my hopes up – only to be disappointed. I was slowly becoming convinced that for whatever reason I was never going to get married.

Despite everything, I did meet an amazing woman and we recently got married. I learned a lot along the journey to the chuppah and have observed what many singles seem to be doing right… and wrong. In the interest of helping others cut down on the wear and tear of being single, here are some pieces of advice for older single guys (and probably many younger guys as well):

1. Get back into the race. What choice is there?

More times than I care to remember, I went out on first or second dates that I thought were terrific only to find out the woman thought otherwise. When I found out the “bad news” I would feel as if I’d been kicked in the stomach. Inevitably I’d call my rabbi. I’d tell him what was going on and unload the full weight of my being single. It was usually pretty depressing and melodramatic.

What my rabbi sang to me was closer to reality than my over-the-top sense that there was no hope.

He’d listen carefully and be sympathetic, but then (and I kid you not) he’d sing me lyrics from Frank Sinatra's That's Life: “I pick myself up and get back in the race.” He did this every time. I can’t say I was thrilled the first few times; it didn’t match the terrible state I felt I was in. But eventually I realized that what my rabbi sang to me was much closer to reality than my over-the-top sense that there was no hope. I needed to just keep going, and while I might be a bit down or need a short break, there was no choice but to get back into the race.

2. Have “turnkey” date plans ready

I had way too much going on my life to constantly think of amazing new dates all the time. If you like finding new things to do, then by all means, go for it. But if being a social activities director is a bit much for you, have a few set date ideas that you know work. Examples: a Starbucks date (in a Starbucks that you know has seating available) or a miniature golf date etc. Make it easy on yourself. As long as you offer your date a reasonable option or two, in general she’ll be happy with the choices. Keep in mind that the main point of the date is to get to know your date – not to try out every single dating possibility on earth or to show how creative you are.

3. If you're dating to get married, then act like it

Remember why you are dating and what the purpose of a date is. Don’t just go out and hang out over and over again. While the date can be fun – just make sure you are learning about the woman you are dating. Have an idea of what you want to ask and what you want to learn about her. Otherwise, you may go out several times and still not know each other much better than you did after the first or second date.

4. Be forgiving

Dating requires having a thick skin. When you have been dating for a long time, you can become overly sensitive to slights and insults, imagined or real. So try to have a forgiving attitude. If your date doesn’t say exactly the appropriate thing, let it go. This doesn’t mean you have to become a doormat (never a good idea!). But don't turn the tiniest offhanded comment into a big deal.

5. Be willing to do what it takes

To find my wife, I needed to be willing to do whatever it took. If that meant traveling, I traveled. If it meant going to someone’s house for a Shabbos meal, I went. If it meant going to a matchmaker, I went. Trust me, I didn’t like doing all this stuff. But I realized I needed to do my part in the process. It wasn’t easy. It wasn’t always cheap or fun. But it eventually led to meeting my wife. It was worth it.

6. Slow down there, Bucko

If you met a woman you like, that's fantastic. Now build on it. Many guys dating a woman prematurely roll out a laundry list of all their problems, weaknesses and “issues.” Would you do this with a new client or with a new colleague at work? While there are exceptions, the third date is not a signal to let down your guard and spill your guts about your deepest feelings and fears. It is a bit early, to say the least. Women may listen sympathetically and even be quite involved in the conversation, but that does not mean it makes them like you more or feel closer to you. It's a bit immodest to share so much so quickly; it creates a false intimacy. It's like microwaving a fine dish that really needs slower cooking.

Yes you need to share, but unpeel the onion slowly.

When we talk about other parts of our lives (work, shul etc.) we're usually positive, upbeat and have a “can do” attitude. Have that attitude about yourself on dates. I am not suggesting lying or being closed. I am suggesting that you pace yourself. No need to spill your guts about negative stuff early on.

Yes, you need to share – how else are you going to connect with a woman? But make sure to unpeel the onion slowly.

7. Listen to what women tell you about dating

Women told me that they did not like going out without being told beforehand whether they were going to dinner or not (they didn’t care either way, but would eat beforehand if they knew to do so). They didn’t like going out (the first few dates) with a guy who had no plan for the date. They preferred being given an option on a date (would you like to go here….or there?). If women in your life give you advice about dating – listen. Chances are it will very helpful.

8. Despite it all, have fun in your life and on dates too

Yes, it is tough being an older single. Okay, next topic. That really needs to be your approach (except for the conversations you have with your closest friends). People will listen, they’ll smile, but you gain very little by becoming the raging single that spews forth about terrible first dates, awful matchmakers and evil dating websites. You’ll sound bitter, you'll become bitter, and you will be concentrating on the tough things in your life rather than the sweeter things.

Sharing a funny anecdote is fine, but don't become a complainer.

Instead of focusing on what's missing, enjoy life, do fun and meaningful things. Don’t wait for marriage to give you permission to vacation, to volunteer, to host people….whatever it is. And enjoy your date. After all, women are a lot more attracted to someone happy and upbeat.

While you're dating you are on a waiting list to get married… so make sure to enjoy the wait. And keep in mind a quote from Winston Churchill which kept me going: “Never, never, never, never give up.”

October 3, 2010

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Visitor Comments: 59

(46) steve gitahi, November 9, 2012 12:23 PM

i like your comment

(45) Anonymous, November 5, 2012 12:35 AM

age issues

The biggest problem Jewish women in their forties face is that while our contemporaries want much younger women so they can have more kids, we are too young to be interested in men in their sixties who seem to be are looking for a nurse in their old age, not love. What I have found is that I can get along beautifully with men my age, on many levels, but they are holding out for a younger one. It is very depressing. It's why I have stopped dating, basically.

l, November 7, 2012 8:10 PM


completely agree- or they are gloing through their andorpause... and feel entitled to 'something', not sure what?? lol.

Anonymous, June 10, 2016 6:44 PM

keep dating...

there are plenty of over 40 women that get married to men their age or slightly older or slightly younger. The Midrash speaks about when the Jews were living in the dessert, there were 2 daughters of a land owner who were well into their 40's and unmarried, came up to Moshe Rabainu to ask them of their inheritance of their fathers land since his passing. Their husbands would of inherited the land for them, but since they werent married it was a big question. Who would receive this fortune? they were unmarried, and about to lose a wealth of inheritance, and were basically laughed at for asking such a question. Becuase of their dedication to the law , H rewarded them to not only marry but married top notch scholars and received all the inheritance of the land. DON'T GIVE UP. keep going. and trust me, some men don't care about younger as long as the personality is fitting to them.

(44) scott, November 2, 2012 8:04 AM

Good Advice

My wife and I met and married at 40. We have since made aliyah and have a baby daughter. We're starting a business together and having a blast. I too had to revamp my dating skills in my 30s. Most of what he says is true. But the thing that helped me the most was to understand the structure of dating. First date-the guy asked and he's interested. He's Mr. Yes looking for reason to say yes. The woman...well it wasn't her idea and well she's not looking for yes. She's looking for a reason to say no. She's looking for what's wrong with her date. And if she says yes her single friends are looking for a reason to trash her's a sad fact of woman-woman relationships. He single friends want her to stay single lest they be left out. And on the first date, she'll use any excuse to say no. Don't give her one. Dress appropriately, have a plan, smile, keep the conversation completely positive and casual, pick up the check, open doors-all that stuff. Do not take the bus or subway. As the dating progresses and she lets her guard down, then let her know more of what's really going on in life. But here's the thing-trade negative points over time. She tells-or shows you one then you show her one, not two or three...She's always looking for a reason to say no. Most alpha type 30 something women-no matter how much they say they want to be married-don't really want to make the compromises that marriage entails. My wife viewed marriage as a sort of death-I have to travel and have fun and pursue my career and financial objectives before I marry, because after I do, that's all over. Thank Hashem we met, because if we hadn't she'd have all these important things but never gotten to meet her daughter. What a waste. And the funny thing is we have more fun and have had more adventures in the four years since we got married than in the previous forty. But I had to do it by always remembering that she unconsciously was looking for a way out the whole time.

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