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Hi Tamar,

I have no idea how to start a conversation with someone I’m interested in. What should I say that’s not too much… but just enough.

Thank you,

Lost in Conversation

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Hi Lost in Conversation,

Great question! Interestingly, when both people are already intrigued by the other’s profile, it really doesn’t matter how you start the email as long as you take the time to send one. That said, here is an example that you can play around with and personalize:

Hi there,

I was attracted to your profile by your photos, but I was really impressed by what you wrote, especially _____________. We have a lot in common (which you can see by reading my profile) and I’m always excited to meet people who also love ________________. Have you ever ________________?

Looking forward to hearing from you,

Sam

Hi Tamar,

Can you please tell me if my pictures or profile needs a make-over?

-Photo Perplexed ____________________________________________________________________________________

Hi Photo Perplexed,

I really liked what you wrote in your profile and you answered the questions quite nicely. You could go back and fix some typos, but I like what you had to say and found that you described yourself and what you’re looking for quite well. You seem to be true to yourself, and it is endearing.

I wasn’t as impressed by your photos; my initial reaction was that they are not “naturally you.” I do recommend going on photo shoots, but it’s not ideal when it is obvious you are posing for a camera. I advise deleting all the photos except for the 2nd one and the last one while you take or find new ones.

The other thing that I didn’t really like is that you aren’t smiling in any of the photos! The lack of a smile makes it seem like you are not as approachable as your profile makes you out to be. Whether it is a friend or a professional photographer, ask someone to take photos of you in a natural, organic setting (not posing, not in front of a white screen), somewhere that shows you relaxed and enjoying life!

What is love? Well, it’s not an easy thing to define, that’s for sure! Feelings never are. Perhaps it’s easier to describe what it’s not. Love is not attraction, and it’s not sex. Love is not wanting what you can’t have or missing someone when they’re away. All those things belong in the camp of lust. Are attraction, sex and missing each other important? Yes. But, it’s not what love is.

Every relationship is different, but each has to have some basic fundamentals. Love comes from building a foundation of trust, friendship, compassion, and being partners in (and sometimes against) life. Without these key elements you may like someone, and you may love being with them or love certain things about them, but you don’t have enough to survive.

It takes time to build this foundation but it is integral to the process. This doesn’t mean to run away from what I described as lust; it just means not to confuse the two, and to give love time to develop. It can take time to solidify, so try to be patient as some people need more time to be certain those elements are deeply rooted. Falling in love feels so good, it gives us a euphoric high, but that feeling can also confuse us from seeing signs that the building blocks are missing or crumbling before our very eyes.

Finding love isn’t easy, but it’s why you are on 100hookup – to look for it – so don’t give up! It may be frustrating, but it’s better to stay single than to enter a loveless relationship just for the sake of being in one.

100hookuprs are not shy about sharing their opinions — and the strongest and most popular one I get is about age. Check out a few of the emails I’ve received:

“I, at age 57, have had mostly older people (by 10 years) reach out to me. Even when I expressed that was too old because it was a different generation, a man lied and said he was 67. When I met him, he admitted to being 77. Don’t people ( I know women lie too) realize that once a lie is admitted you can’t start a relationship  with trust?”

“Tamar have you checked out the wishes of many men who qualify as one foot in the grave and one foot in a nursing home? Somehow I think these men have not looked in a mirror for at least forty years. When I see a 76-year-old gentleman looking for a woman 20-40, it gets me very nervous. The problem is these men have an overinflated idea of their looks and an underinflated idea of their age.”

I will advise this until I’m blue in the face: don’t lie about your age if you are serious about meeting someone because they will find out your real age eventually — so why fib about it to begin with? Just like the first 100hookupr above wrote, starting off with a lie is not a great way to build a successful relationship. That said, your preferred age range is just as important.

A ten-year gap is a general rule of thumb, but of course there are exceptions to that. If you are looking for someone more than twenty years older or younger than you, then I strongly encourage you to rethink what it is you are truly looking for in a partner and in a relationship.  

You gotta know how to treat me like a lady
Even when I’m acting crazy
Tell me everything’s alright
-from Meghan Trainor’s new single “Dear Future Husband”

Women (in general, it’s women) are often called the “c” word… get your mind out of the gutter, I’m talking about the word “crazy.” It gets thrown around pretty flippantly and it’s incredibly disrespectful. And, ironically enough, it is usually the action of the man (in general, it’s the man) that causes the woman to lose her cool and then to be called crazy by said man (again, this is a generalization). It’s enough to make your head spin.

Everyone acts crazy every once in a while. There’s a reason why so many love songs have the word “crazy” in them (Google it!). Love makes you do crazy things, feel crazy ways, and act crazy in love. Let’s remove using the word “crazy” as an insult from our vocabulary while dating… and continue the ban once you’re in a relationship. It’s not going to go anywhere good if you sling that word around!

Frankly, ‘crazy’ is also too broad of a description when you are describing a person’s reaction or an event. Let’s find other words in the dictionary to use, shall we? I don’t care if you have to pause and consult a thesaurus mid-argument, find other words that will likely better describe the situation. And then, when things really do get crazy — like the girl who got dumped and cracked open her ex-boyfriend’s patio door, slid the garden hose in, turned on the water, and left… or the guy who was cheated on and then poured milk under his ex-girlfriend’s driver seat (she didn’t even know what happened until weeks later, ewwwww!) — you can use the word “crazy” and not only will you actually mean it, but people will take you seriously.

And by the way, when we women use the word crazy to describe ourselves, we would appreciate you telling us that we are justified in our behavior! You will earn major points for that!

When you are newly dating someone it is NOT the time to discuss the drama in your life, nor is it the time to whine and complain about things in your life. I’m not saying to make everything sound wonderful and perfect, but don’t turn a date negative with your stories about how your friends are fighting, or your siblings aren’t speaking to each other, or your job sucks, or… or… or…

There’s the normal vent about your computer crashing before you had a chance to back it up one last time, but spend about a minute on things like that and move on. That type of vent is something everyone can relate to and empathize with — and may even have advice to help you. If the dating turns into a serious relationship then you will have plenty of time to be the sounding board for drama!

You know how it is… you’re on a first date and you are telling the person sitting across from you all the positive things going on in your life that will impress them, possibly even embellishing things. You make your job sound exciting with a promotion just around the corner, or you portray your family as tight-knit and easy-going, or mention all your best friends and your packed social life.

And your date is impressed by the idea that you have it together and so you get a second date, and a third, and then eventually you are meshing your date and your reality… which is a job you hate and a promotion you’ve been waiting for a year already, or a family that is just as drama-filled as every other family out there, and a few great friends but with most nights spent at home alone (which is perfectly fine).

None of these things are abnormal, but when you’ve presented yourself as something other than what you are, then you’re going to have a lot of ‘splaining to do, Lucy! All kidding aside, you are going to have to find a way to bridge the gap between what you portrayed your life as… and what the reality is.

Instead, mix the two together from the start. Everyone embellishes, just do so in a way that you won’t bite you in the tuchus later. For example: “I don’t love where I am with my career right now, but I’m excited that a promotion is coming soon” and “I love my family and we are always there for each other at a moment’s notice, but sometimes they make me want to beat my head against a wall!” and “I’ve learned that friendships are quantity or quality, and I truly adore my friends and their loyalty… and the trouble we get into together!”

Illinois Lady claiming to not be photogenic got me thinking about judging a book by its cover. Should her prospects not contact her because she only has one photo that is nice, but not stunning? Or should they contact her because her profile is pretty great? Does one element outweigh the other? Do you need both? Do you chance that the person who has a great profile could possibly be like “Illinois Lady”  — i.e. not photogenic, but someone who impresses you once you actually meet in person? And then perhaps once you meet, you will be so impressed that you are even more into them because your attraction is based on more than purely physical or sexual factors? What do you guys think?

Dear Tamar,

I just joined 100hookup in January and I am getting mixed responses, mostly from older men that are unattractive or weird. Can you take a look at my profile and photo to tell me if something is not working? Everyone tells me that I look much prettier in person, so photos are always a dilemma for me. Please advise. I would also like to spice up my profile name as well!

-Illinois Lady

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Dear Illinois Lady,

Your profile is well-written and complete, but perhaps too polished. You clearly know who you are, which is awesome! I would simplify your profile because men may wonder how they can fit into someone’s life who clearly has it all together (whether you do or not, it seems that way). Confidence is sexy, and I’m not telling you to appear less so, just to not sound so sure of everything.

There is a bit of repetition, and as I advise in my book “How to Woo a Jew” there is no need to answer every question if it means repeating the same answer over and over. You mention the Chicago Botanical Gardens a few times — as well as being outdoors, feeling free to contact you, and traveling. I understand that these things are important to you, but it’s redundant, and when people are skimming through a profile things like that can be a turn-off.

As you know, you need more photos. It’s tough when you’re better looking in person, but it’s worse when you’re not as good looking as your photos! So snap away and get some photo-ops in and upload a few photos that your trusted confidants agree looks the most like you.

As for your profile name, right now you have your name and what I assume is your birthday. It’s not a bad profile name, but you could do better. There is mixed thought on using your actual name as your profile name — on one hand, it gives off a sense of familiarity, but on the other hand it may not be the smartest in the sense of security. Make a list of adjectives and nouns that describe you: what you look like, what you do, your hobbies, where you live, and so on, and then try to combine two of the words into a catchy profile name. Try not to use your age, since you will eventually have a birthday and then your profile name will be moot.

I think you’re very close to having a really great profile! Once you have revamped your profile, go through your search results and view the guys you match with so they know you’ve viewed them and are possibly interested in seeing if there’s more.

Dear Tamar,

I read all the tips on how to send that first email to ladies. I also emailed more than a dozen ladies on 100hookup and not one of them responded. I think the fact that I am shy and inexperienced may have something to do with it, but I’m not sure. Here is the email that I sent to the ladies on 100hookup:

100hookup.com probably thinks our profiles matched so I’m sending you this email. It is cool. If you are interested in continuing this research, please write me back when you have a chance.
Best Wishes,
xxx

Do you have any advice for me as to how I can change this email? Or maybe something I can put in this email so that when I email the ladies on the website they will respond to me? Please let me know. Have a good day and I look forward to speaking/hearing from you soon.

Best Wishes,
xxx

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Dear Inexperienced Emailer:

You weren’t kidding when you said you were inexperienced! Your email is awkward, stiff, and, well, awkward. Emails to prospective dates should not be so formal, or appear to be copy/pasted, or appear to be written by Google translate for that matter.

Since you are writing to a prospect on 100hookup they know that something attracted you to them — so what was it aside from being told you’re a match? You shouldn’t be writing every single prospect an email, only the ones who fit the majority of your preferences and whom you’re attracted to. That said, you should write what it is that you’re attracted to that made the prospect worthy of your time and effort to write the email.

End the short email with a question that addresses something in their profile and shows that you want to get to know them better. You need to prove that you actually looked at their profile by writing both with a compliment and a question, being conversational and casual, and adding in a somewhat flirt tone as well.

Good luck!