May-December Romance

by Tamar Caspi under Relationships

Dear Tamar,

I have been approached on JDate by much younger men and it confuses me.  I am widowed and, for me, the comfort of being with a widower makes wonderful sense so I’m sad to see that some of these men are this much younger than I and with a loss already.  There is someone that I feel a connection with at this time and I’m nervous that he neglected to see my age. Is this younger man/older woman (Ashton and Demi) becoming trendier?  I’m battling grey hairs and wrinkles!

Dear May-December Romance,

There is no way that age can be ignored on JDate, so believe me this guy knows EXACTLY how old you are and he likes it! Age is one of the first things people look at and next to location it’s probably the most utilized tool to separate your prospects.  It sounds like you’re a hot widow that looks young for her age and is doing a great job battling the gray hairs and wrinkles! Your youthful appeal is probably also emanating from the inside out, so enjoy the attention and be open to the possibility of falling in love with a younger man!

Waiting To Be a Widow

by Tamar Caspi under Relationships

Dear Tamar,

I’m nearly 60 and my wife is terminally ill with cancer, living with round-the-clock nursing care under home hospice. I’m on an emotional roller coaster which levels out when I have contact with people outside of my home. That said, I’ve been trying to meet women on JDate for very casual meetings, but as soon as I describe my situation, I become radioactive. Should I stay home til she dies? Make up a different story? Can you think of a way I can explain this without scaring people away?

Dear Waiting to be a Widow,

I think any woman would cringe upon hearing your story and understandably so. Your wife, although dying (and my sincerest condolences, I hope she’s not suffering), is still alive. I’m not sure JDate is the place for you right this minute, but once you’re done grieving it’s a different story, because honestly I don’t think there’s any way to describe your situation without scaring people away. Try to put yourself in their shoes — if you heard your story out of a woman’s mouth you would be scared, too. I hope you find people to socialize with outside the home to help you keep your sanity and I hope you one day find someone on JDate to spend the rest of your life with.

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Never Too Late for JDate

by Tamar Caspi under Relationships

Dear Tamar,

How realistic is JDate for a widow aged 68? Reading that a 5% response rate is not bad in general, how does this hold up for a woman of my age? It’s hard not to be discouraged because no one has expressed any interest in me but it would help to understand the odds better. I know there are enough men over 60, but how many of them will even consider a same aged woman?

Dear Never Too Late for JDate,

In general, the odds may seem to be against you as women outlive men. But don’t let that get you down. Instead, use JDate to your advantage by expanding on the possibilities of meeting an older man, a younger man, or even a man who lives in another city. Play around with your preferences and by that I mean make them as wide and broad as possible. Don’t limit yourself (okay, well, limit yourself to a point, but be flexible). Even if your hobbies and interests don’t overlap, don’t count the guy out — you may still enjoy his company! A minimum age range is understandable, but there are plenty of youthful and active 75-year-old men out there so don’t count those guys out! In addition, don’t forget to get involved in activities in your community because the same guy who may have overlooked you on JDate may see something he missed when he sees you in person.

Creep or Compatible?

by Tamar Caspi under Relationships

Dear Tamar,

I’m 59 and my wife died about a year and a half ago. It seems like every other day I get another JDate Match sent to me of women who are between the age of 35 and 40. Some are pretty attractive! I just keep thinking that if I express interest in any one of them, I’ll come off as some creepy, lecherous, old guy.  Help me out here- is this just in my head or is it just outright creepy?

Dear Creep or Compatible,

I appreciate your concern for not wanting to come off as a creep. There is quite a difference in life experience between a 59-year-old widow and a 35-year-old single. JDate matches are sent to you based off of the preferences you both set, so if you want to find out about women a few years older than you, you need to change your age range settings. Once you do that, you need to check the preferences of the matches you’re receiving by scrolling down to the bottom of their profiles to see if you fit into their age range and marital status choices. There must be something you have in common which is why you got the match sent to you, but both of you having a dog and living in the same zip code does not a shidduch make. If you do find that you have many commonalities then it won’t hurt to send an email saying both that you seem to have a lot in common and that you hope you’re not coming off as overachieving (try not to use the word “creep” in a first email). The worst that will happen is that you won’t hear back. Good Luck!

83 Years Young

by Tamar Caspi under JDate,Online Dating,Relationships,Single Life

Dear Tamar,

I am a widow, 83 years old, slender, active, attractive and independent.  I am sad because I lost the love of my life and fear I will never find anyone else who is open to pursuing the art of love and living as much as I do. I am uncomfortable telling my age, except to my doctor and other confidants, because I believe there is such a stigma attached to this number.  Any advice?

Dear 83 Years Young,

I couldn’t help but laugh out loud when I read your email. My Grandmother, who is 81, tells people she is 36, not because she expects them to believe her (although she does look amazing), but because to her age is a state of mind and saying she’s 36 keeps her feeling young and healthy. At the same time though, once my Grandmother had her 80th birthday she began telling people her real age because she was proud of it and knew she looked darn good! So I see it both ways. Since you’re looking for people around your same age to spend the rest of your life with, “pursuing the art of love and living,” I don’t think JDate is the place to be lying about your age. Embrace it and you will attract men who are also active and independent. Make sure your age range preference shows what ages you’d be realistically interested in meeting and do your homework as well — use the search function to find men around your age who have similar interests. Good Luck!

True Love Take 2

by Tamar Caspi under JDate,Online Dating,Relationships,Single Life

Dear Tamar,

Do you think after spending 39 years with your Beshert, there is another one out there?  I am a young-ish widow (58 years old) and wonder if I will spend the remainder of my life without that type of love again.

Dear True Love Take 2,

First, I am sorry for your loss. Losing my spouse at a young age is one of my worst nightmares. My parents have friends in this situation as well, and I’ve fully supported them in signing up for JDate, attending temple functions and going on blind dates. You are young, active, and could have 40 more years of living to do (knock on wood) and want someone to share that with. Totally understandable!  That said, I do think it’s possible to find true love again! Not only do I believe in there being more than one Beshert for each of us, but I believe that once we’re in a different stage of our lives — as you are — our idea of who or what defines a Beshert is different from our definition when we were much younger.  Just think, compared to 39 years ago, your list of preferences is so much simpler — you’re not worried about finishing college, having kids, buying your first place, getting a job that will support your growing family and so forth. You’re probably more concerned with sharing the same interests in movies, food, traveling, and spending time with grandchildren. Keep your JDate preferences as broad as possible and let your friends, family, Rabbi and virtually everyone you come in contact with know that you’re interested in being set-up. Good luck!

Turning Sadness into a Second Chance

by Tamar Caspi under JDate,Online Dating,Relationships,Single Life

Dear Tamar,

I had a fairytale marriage — I got married the day after high school and had the absolute dream husband. Sadly, he passed away in 2006 after 23 years together.  I can’t or won’t ever forget him but I don’t think men will want to discuss him. He is obviously a part of my life that I will always cherish (an added bonus is that my 19 year old son looks exactly like him). How do I approach this delicate situation?

Dear Sadness to Second Chance,

First, I am so sorry about your loss. It sounds like you had an amazing marriage that most of us can only dream of and no one will ever fill your husband’s shoes. That said, you are right — men you date probably won’t want to talk about him, at least not right away. I think you need to be honest and mark your JDate profile as “widowed.” When asked, tell men you plan to date that you’ll be happy to share your story at a later time once things progress. Let them know that you are in a good place now and ready to date and meet someone to share the rest of your life with (or share quality time with, depending on what it is you are looking for), so that men won’t have to worry about your emotional state. Everyone out there has some sort of “baggage,” especially, and I don’t mean any offense here, the older you are.


by GemsFromJen under JBloggers,Online Dating,Relationships

Dear Gems from Jen,

I met a very nice man on JDate who lost his wife 18 months ago. He said that he still loves his wife, and he feels that we have a great potential, but at the same time he feels that he met me a little too soon. Sometimes I feel that he pushes me away and then the next day he shows me deep affection. He is the only man between all my dates that I really like, but I do not know how to handle this situation. I need your direction.

Dear Widower,

This has got to be a very confusing situation not just for you, but for him as well. You are receiving very mixed messages, which tend to lead to hurt feelings and unrealistic expectations. It sounds as if he has made it clear with his words, but not so clear with his actions. It does appear from what you have told me as if he is still somewhere in the grieving process. My best suggestion would be to have a completely honest conversation with this man. Let him know how you are truly feeling and ask him what it is he is looking for in terms of a relationship with you. You will have to make a decision if you are willing to meet him where he is at. He may not be ready for a serious, committed relationship. If you are looking for this type of relationship, you may need to make the decision to find someone who is ready. Pushing him into something that he is not ready for will only backfire. Do yourself a favor and make sure if you choose to stick it out with this guy you look at all of the different outcomes. Keep in mind your feelings are just as important as his.

Gems from Jen

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