10 Answers on Dating, Sex, Age, Gender, Religion, Faith, Sobriety, and Rules

By M. Alexander

This week, I have spent a lot of time speaking with Ilana Angel, writer of “Keeping the Faith”, The Jewish Journal’s most popular blog.  Ilana writes a lot about dating—she is a single, 45 year old mother.  I am a single, 22 year old recovering heroin addict.  We began to discuss dating, relationships, and sex—immediately realizing our many differences. She called me “Pig.”  I called her “Neurotic.”  We decided to each answer a series of dating-related questions—are we really so different?



MICHAEL: Sometimes I think, “Damn, I’m handsome, smart, and charming.  If she doesn’t fall for me, she’s probably dense and blind.”  Other times I think “What was she thinking when she agreed to go out with me?  She probably just wants a free dinner.  She probably feels bad for me.”

But I’m becoming more successful at clearing my mind before a date.  I usually stay busy until right before I have to leave, attempting to go into a date without anxiety.  I try not to judge myself or judge my date as either prettier than me, dumber than me, or more desperate than me.

If I go into the date without expectations and let things flow effortlessly, everything usually goes smoothly.  I can then be more honest about whether or not we have a connection and we can mutually decide whether we want to see each other again.

ILANA: I case the joint for emergency exits, make sure I have a girlfriend scheduled to call me 30 minutes in should I need an emergency exit, pray to God I have not made a bad decision and am about to meet someone unsafe, order a drink, pop a TicTac and hope for the best.


MICHAEL: I don’t have any pre-set guideline.  If the girl wants to wait 3 months, I’ll wait three months.  If the first date naturally leads to immediate sex, I am not going to throw her off of me.

ILANA:  I have waited and not waited and it does not change how I feel about myself, or the man I am with.  When I was young I was tormented if I slept with someone too soon, but now, in my 40’s, I am more forgiving of myself and allow myself to live and enjoy sex as part of my life.


MICHAEL: I like to think I’m pretty open-minded, but no pre-ops or post-ops.  And if she believes that she was a man in their past life? —I’m not sure what I’d do.  Convicted felons? No problem, as long as she’s interesting.

ILANA:  There are certainly things that I am not interested in at this stage of my life, but I would not categorize them as deal breakers becasuse they are simply not an option.  I only date men who are Jewish, but Jewish is not a deal breaker as much as it is a preference.

I also am not interested in dating a man with young children as my son is getting ready to leave the nest and I want to embrace the freedom.  Again, I would not date someone with really young kids so it’s a preference, not a deal breaker.


MICHAEL: I’d rather meet someone organically. I guess I’m old-school in that respect.  But I am not opposed to dating sites.  I just haven’t gotten to that point yet.  Maybe it is because I don’t want to vulnerably expose myself in a public forum.  No.  That can’t be the reason.  I’m fairly well-practiced in the art of public exposure.  I think I’m just too lazy and have too much false pride to set up a profile.

ILANA:  JDate is a hell train that I will never ride again, and online dating as a whole is a necessary evil.  It can be scary and dangerous, but so is any way you meet someone.  I don’t go to clubs, and I work from home, so I date online because my options are limited.  I have had enough success with it that I am able to continue.  I’ve become a little jaded, but remain hopeful.


MICHAEL:  It depends.  If I ask her out, it is my responsibility to pay.  She agreed to go out with me and I want to show my gratitude and treat her gallantly—I want her to know that I am a gentleman, but I also don’t want to seem like I am just trying to “win” her.

If she asks me out, it is a trickier situation—especially if she chooses the restaurant. I may not be able to afford it.  I’ll make sure that I have enough to cover the tab, but I think she should offer to pay her portion.  Then, I can tell her not to worry about it.  If she insists, I don’t stand in her way.  Instead, I say that I will buy ice cream/coffee after dinner—this stops the fight over the bill and guarantees a dating continuance.

After the first date, it is dependent upon more factors; it becomes more complicated.  Footing the bill is not the only way to show my chivalrous nature—holding the door, listening to what she says, and respecting her boundaries are more gentlemanly than picking up the tab.

ILANA:  If I invite a man out, I will pay.  Most men will not allow it, but I still offer.  If I am asked out, then the man will generally pay.  If asked to go dutch, I will happily pitch in.  Money is never really a discussion or issue when dating at my age.


MICHAEL: I don’t drink.  I am a recovering alcoholic.  But I don’t mind if my date orders something while we are out.  It truly doesn’t bother me.  If it did, I would tell her.  Last night, I went out with someone who ordered a vodka tonic.  I ordered a diet coke.  She asked why I am not drinking and I told her the truth, without trying to shy away or hide.

It didn’t seem to bother her. And if it did, c’est la vie.  It’s better to get it out in the open on the first date than the fifth.  But if you are going out with an alcoholic, I suggest that you respect their disease and don’t drink—at least on the first date.  It is just more respectful.

ILANA:  I am a very lightweight drinker.  Two cocktails and I do not have a clear ability to make the right decisions.  I generally stay away from drinking until I know the man, feel safe, and can relax a little.  On a first date one glass of wine is my limit and I will nurse it over 2 hours.  If I am on a date with someone who does not drink, then neither will I.


MICHAEL: I have a lot in common with many women who are much older than me, just as I have little in common with many women my age.  Maturity is much more important.  I would love to date a 35 year-old woman.  I would also date an 18 year old.  Age is not really an issue.

ILANA:  Yes.  I cannot relax with a man who is much younger than me, or one that is much older than me either.  I am really trying to loosen up on this issue.  I would hate to miss out on a great man because I have a hang up about him being too young or too old.


MICHAEL:  1.  Don’t take it too seriously: it’s a date, not a marriage.  2.  Don’t manipulate: It brings me back to my addiction and it never works in the long run.  3.  Be a good guy.  4.  Don’t make any more rules.

ILANA:  1.  Take it seriously, it could be your last first date.  2.  Trust my gut.  3.  Be a lady.  4.  Follow the rules.


MICHAEL: I don’t make much money.  If a woman judges me based upon the amount of money I spend, she is not someone I should be with.  We can eat good food in a pleasant atmosphere and do something fun afterward all for under $40 dollars.  If Rachel Ray can eat for under $40 a day, I can certainly charm someone without much money.  The best dates I’ve been on have been the cheapest.  I don’t know if it’s coincidence or not.  But when I spend more money, the date seems to be worse.  I don’t want to buy her, I want to charm her.

ILANA:  It does not matter, just have a good time.  If he can’t pay, I can.


MICHAEL:  Faith and religion do not come into play when I am casually dating somebody.  I can connect with an atheist just as easily as I can connect with a Jew. Any faith or religion is fine, just as long as she’s not radical or fundamentalist (though it might be fun to date a cult-leader for a couple weeks).  I haven’t ever had a serious relationship so I honestly can’t say whether religion or faith would become important.  I want her to have purpose and passion more than I want her to believe in God.

ILANA:  Faith and religion are important. That said, faith trumps religion.  I could not go out with someone who did not believe in God.  He must be Jewish, but he does not need to practice as I do, or have the same worldview, but he must have a belief in something greater than himself.

I feel a connection to Judaism, and am raising a young boy to be a man.  It is a tough job and if someone is going to be in my life, and have the blessing of knowing my son and being in his life, he should be able to share in our faith and help me to present Judaism to my son in a way that he embraces it.


Ilana and I are both searching for attraction, love, and connection—but the way we seek it is quite different.  I believe our differences are best summed up under Dating Rule Number 1.  My first dating rule is “Don’t take it too seriously.”  Ilana’s first dating rule is “Take it seriously.”

We are living in different worlds.

Ilana’s World: Lovelorn Fairy-tale Princess Seeks Beshert.

My World: Recovering Heroin Addict Tries To Live Life

Yes. Our worlds intersect.  But the overlapping section of the Venn Diagram is still a small space in comparison to the parts that are diametrically opposed. We are quite different, but since I’ve been spending time with Ilana Angel, I am trying to keep the faith.

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2 thoughts on “10 Answers on Dating, Sex, Age, Gender, Religion, Faith, Sobriety, and Rules

  1. Susan (Bell) Rifkin May 13, 2011 — 9:01 am

    Michael, I loved this post. As a remarried woman closer to Ilana’s age, with a son in his 20’s and in recovery, I can see both sides. I appreciate your comment about living life in a healthy way, and certainly relationships are a big part of that. So just keep it real and honest; the rest falls into place.

  2. Susan,

    Thank you for your comment. I try to keep it as honest as possible. Hopefully, things will fall into place…eventually.


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