Michael Asked:

“I’m a gay man who got out of his first relationship (almost three years long) a few months ago. It was a great relationship, and ended on amicable terms, and we’re still best friends now… however I think it spoiled me and I have a major problem! I don’t know how to date!

Let me give a little background to clarify:

Michael (ironic that he has the same name as me, isn’t it?) and I met at first and our relationship was not a relationship until a few months in we noticed ‘hey… we’re dating, aren’t we?’ and by then we knew each other so well that it didn’t even matter. We were best friends, but there was that spark of romance that neither of us had noticed (or acted on) until the day we sat and talked about it.

So here’s my problem! I don’t know how to date… specifically I don’t know how to ask guys out, I don’t know how to go through that whole ‘beginning’ relationship phase (since my only relationship effectively skipped it), and I don’t really know how to jumpstart everything.

I’m not looking for some sort of ‘hot and heavy’ commitment-ful relationship, however, I’m not really looking for a fling either. The great thing about my last relationship was that it was really light, but we were very serious at the same time. We were even talking about getting married (or whatever you want to call it) and ‘the rest of our lives’ and everything. What I want out of a relationship is something that is light, silly, and a little unserious on the outside, but that is based on a firm, deep commitment.

Am I hoping for the holy grail?”

- Michael

Our Experts Responded:

Dear Michael,

Congratulations on a wonderful Journey that ended with you and your ex-life partner remaining best friends. I am often amazed as most, when we hear about relationships actually lasting into the golden years and in today’s World being married over 60 plus years, oh man not always easy I hear. To end the lover part of the relationship, actually let go and remain best friends leaves me with hope.

You met this wonderful man and a spark of romance bonded you as lovers and friends naturally. He was meant to be a part of your life, reasons that only you will understand in your lifetime. Was your first gay relationship supposed to be this natural, so caring and nurturing? I believe so because he is who you needed at that time in your life, he is who you asked for.

You’ve asked for a relationship that is “light, silly, and a little unserious on the outside, but is based on a firm, deep commitment.” Kind of like the last relationship?

When we are in long term relationships we tend to pick up likes and dislikes of our partners because we want to be around them. They don’t like scrambled eggs, so you didn’t enjoy scrambled eggs; you went to action movies, even though you’d rather be busting a gut in the theater next door. Reinvent yourself. Who are you and what do you like too do? Remember your dreams and visions?

Hang out in places and with people that have your same visions and goals, you will attract friends naturally and romance will find you…when it is suppose to happen. When the right person walks into the room, you will feel excitement, lust and that feeling as if you are about to throw up and you’ll know what to say and do…it will come naturally.

Drink plentiful from the Holy Grail my friend…Cheers!

Blessings on your Journey,

- Teresa Caravalho Jeanminette

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Michael,

First off, congratulations on having a wonderful relationship and ending it amicably! I also think it’s great that you know what you’re looking for–something light and silly that has the deeper commitment behind it. Knowing what you want is half the battle and it’s definitely not the Holy Grail. A wonderful partner who can offer you what you need is out there longing for you as much as you’re longing for him.

To ask guys out might initially take some planning. Check out websites of great pick-up lines, choose a few that you can say without cracking up, target the places you think you’ll meet a person who’s that great combination of depth and light, and then go out and practice. And the real secret is to not take it seriously. You can’t say the wrong thing to the right guy!

You took the back door into your last relationship—which is one of the great ways to find true love in a partnership. Now you get to try a different route and you’ll do great. The best thing about dating is that gives you a chance to get to know yourself better. Dating is challenging for everyone, but it can be very rewarding. Take a deep breath and relax. Each day you interact with potential partners, you are getting closer to the person who can fulfill you. And your ideal partner is definitely out there waiting for you!

Thanks,
- Marian Lindner

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Michael,

Your predicament isn’t a new one, so don’t feel like you are the only one with these trepidations. “Dating” can be tricky at best, and daunting to say the least. It used to be that meeting people was the hardest part, almost. We’d rely on chance encounters, weighing the options and possible outcomes. Wondering, “Should I go the bar/club route, or simply bump into someone’s cart at Whole Foods?” But thankfully, things are a bit easier now. Not to sound like a commercial for this site, but the internet has made that aspect so much easier, and less nerve racking. You can talk with people, discuss your hopes and fears, and hopefully find enough commonality to encourage you both to take it to the next level and meet in person. But if it’s not a match, then it’s no big deal, either. ” Nothing ventured, nothing gained,” is the hallmark here. Just remember that the other person is most likely just as nervous and feeling just as awkward as you are, so just try to enjoy the process and not put too much pressure on yourself.

The thing to try to remember is that you control your world to a larger extent than you realize. YOU decide how “heavy” the situation is to get, YOU decide if you are comfortable, and YOU decide what you want, in general. If at any point you don’t feel like the situation is what you want for yourself, simply make your exit. But you also decide how much you require, and I applaud you for that.

Society loves to make people think that they are asking for too much. The “Holy Grail” as you referred to it, I think. But without standards, without a utopia to shoot for, we end up simply settling for whatever comes along. It doesn’t take much effort to look at the lives of friends and co-workers and find examples of the many downsides of “settling.” The key is to shoot for what you want, and at the same time keeping an open mind. Find the situation and the pairing that makes you comfortable. This may not always be in the exact path or package that you predict, but it’s out there. If you feel like “Friends First” is what made your last relationship work for you, then make that known. (Just don’t be surprised if as soon as you make that proclamation that you instantly fall for someone purely on a physical attraction level, making you realize that these are only guidelines, but that the cosmos has it’s own ideas sometimes as to how we all find each other.) But in all honesty, regarding the “Friends First” mentality; you’d be surprised I’m sure, that a lot of people feel the same way. No one wants to get hurt, no one wants to throw their heart out there to be stepped on. Playing it cautious, yet with an open mind sounds like the perfect way to get back out there. The rest will fall together.

As for the mechanics of dating; don’t sweat that, either. If you want to find commonality, then simply approach “prospectives” with the same attitude with which you’d like to be dealt. You can’t go wrong with Golden Rule type thinking, right? One quick dating rule though, and I’ll leave you to your own devises. Keep the subject off yourself as much as possible, and let the other person talk about themselves. This accomplishes two things. You learn a lot about the other person, and they are more at ease, as most people like to talk about themselves.

Best of luck. I’m sure you’ll do just fine. Remember, you aren’t asking too much. Stick to your guns and go for what you require out of life. You’ll thank yourself later.

R. K. Ford

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Michael,

Absolutely! But even in the quest for the holy grail it’s an adventure along the way, and you can’t expect to find it right away. So here’s your forewarning: you’re going to meet a lot of wrong people, it’ll feel unachievable and you’re probably going to get frustrated and possibly quit at some point. With that being said…go for it! You can only regret what you never chose to do, because at least you know what didn’t work. One of the most exciting things in life is the beginning of relationships, just dating and seeing what’s out there is just plain fun!

Approaching the dating game….you have to be optimistic and know what you’re looking which is seems to me is very straightforward. If you’re honest with yourself on what you don’t want, it’ll be easier for all the poor guys hearts you will break because they don’t want the same as you do. You’ll be surprised to find how many hot and heavy commitments some are looking to find, and the unsurmountable amount of flings and one night stands are out there to be had.

Only you will know your comfort level on going up to somebody, some interesting ideas to consider are dating websites, where you can get to know somebody first. It’s a fun way to go about it because you can talk to so many people, at the same time while you’re having fun doing that chances are you’re going to meet the right person at the right place at the right time. The important thing to remember is to keep your options open and not settle for something you know you don’t want. Just relax, have a good time, and the holy grail will fall into your lap while you’re busy visiting all the hot spots along the way! Because let’s admit it, there’s nothing wrong with exploring the Great Wall of China, the Eiffel tower, or the open countryside of Ireland.

Christina Law

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Michael,

There’s nothing wrong with hoping for the holy grail of dating, Michael. But if you refuse to accept anything less, you’re probably setting yourself up for disappointment. I can see how you might consider yourself spoiled. You experienced the ideal way to enter into a relationship: you just looked up one day and discovered you were in one. And there’s no reason you shouldn’t try that same approach in the future. It worked once, it can work again. But in order to be successful with that approach, you’ll have to be comfortable initially with just enjoying the companionship like you did with your previous relationship. And I would advise you to at all cost avoid appearing desperate. That’s never attractive, and pretty much a universal turn-off.

You also might consider just socializing and appearing available. Though I’m straight, I have gay friends that I used to go out on the town with (I say “used to” because there’s about 900 miles of distance separating us these days) and I would sometimes get asked out. Anybody is always more attractive to potential partners when you’re with somebody, even if it’s just socially. And anyway, who says it’s always you who is supposed to be the one to ask guys out? You may very well get asked for a date simply by being willing and available. But on the other hand, you don’t want your dating strategy to consist solely of waiting for somebody to ask you. And of course asking someone for a date involves risk. That’s just the nature of the beast.

I don’t think you really need to take a “Dating 101″ course, you just need to get some affirmation that you have a lot to offer in a relationship. Your question doesn’t mention your geographic location, but perhaps Sunny Wang, the coordinator for us experts, can hook you up with someone close to you who can look at the specifics of your situation and give you some focused & helpful advice. I am in the Denver, CO area but Advice.Lovedetour.com experts span the width and breadth of the U.S., so chances are there is someone near you with whom you can talk in person. And of course I’d be happy to help you in any way I can.

Regards,

Tracy Aydelott

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Dear Michael,

Let me start by saying that I was in that same exact position with women a few years back. I was extremely shy, non-sociable, self-conscious, and not exactly the best person when it came to making a first impression or asking someone out on a date. A tip of advice that will really help you before you even try to get into the dating game is, as you will find in my guide to a successful relationship (when it is finished and published), is to make a Venn diagram (two circles crisscrossing at the center). You want the circle on the left to be labeled as “Likes,” the right to be “Dislikes,” and the center to be “Tolerable.” To explain “Tolerable” a bit better, it would be qualities that you don’t necessarily like, but can put up with. Under these categories, list properties, both physically and mentally, that fit into each according to your taste. By doing so, you have determined exactly what you want in a male companion. This will come to be extremely useful when you do start achieving phone numbers and even dates.

As for entering the dating scene and being able to score a date, you need to first examine yourself and find out what your most likeable qualities are, as these are, for lack of better terms, what I like to call the “bait.” Now, typically, as most psychologists and such will tell you, in the dating realm, people like to put up a fake front and tell you everything that you want to hear in order to score your heart, and most of them do it subconsciously. Suddenly, months down the line, their third eye opens and they start to present characteristics that you had not seen in them before. I, myself, have seen nothing but confirmation of this theory, and thus, I assume it to be true; however, it is not exactly something that should hold you back from going out to find a date, and it is a tactic that you need to make sure you don’t use. By finding out your most likeable qualities, you can prevent this subconscious strategy from coming into play by making them more apparent, more visible, or in other words, flaunting them. This ensures that their initial attraction to you is for whom you truly are, not what they wish you were, and it saves a lot of heartache down the line if things were to progress into a relationship. Aside from this psychological knowledge benefiting you in the sense that it forces you to be honest with a potential lover, but it also assists in depicting whether someone is a fake or not. For instance, if someone asks you a lot of questions, you answer them, and to every last one they reply, “Me too!” obviously something is a little off, as no two people are exactly the same and want or like the same things, and I would suggest to proceed with caution. If someone is to disagree or offer their own view for about twenty-five percent (one out of four) of your answers or higher, the probability leans more toward them being honest with you.

Many people out there say that you should practice patience and let love come to you, but unfortunately, the majority of the time, that doesn’t work. If everyone in the world were to follow this idea, no one would take the first step, and thus, we’d be saying goodbye to any hope of love in the future. It is because of the common belief in this saying that I am suggesting you attempt to make the first step, or rather, the initial approach. Doing so requires and displays both confidence and an outgoing personality, both of which are considered to be positive traits, and make one more appealing. Before you decide to go talk to them, first make an observation so you don’t begin to chat and draw a blank on a discussion topic. Take notice to their clothes, what they are eating or drinking, what they are doing (if you are in a bar and they are watching TV, see what they are watching), as opening up with a conversation and relating to something they are interested in always makes for a good ice breaker being that it immediately catches their attention. Upon the initial approach, do not just walk up and instantly state your intentions. Instead, calmly smile and introduce yourself, and figure out a way to spark up a conversation using one of your observations about them.

Eventually, things will take a turn from merely a “two strangers’ conversation” to a “conversation between friends,” which is where you can start to delve into their head a little bit. This is where that Venn diagram will come in useful, as you want to start asking or discussing things to figure out which qualities they meet. Should they wind up in the “Dislike” category, that is okay, as there isn’t any problems with meeting or making new friends. On the other hand, if they wind up in the “Like” circle with a few “Tolerable” traits (make sure you don’t have too many of these, as they can lead into dislikes if you find yourself overwhelmingly trying to tolerate too many things at once), you can then begin to come forward a bit with your intentions. At the end of the night, when you are getting ready to part ways, just simply ask if they would like to go out for a drink or a bite to eat sometime, and generally, if they answer with a yes, they will exchange phone numbers (if they don’t, just ask). If they reply with a no, that is not a problem in the least, as you just move onto the next person, rinse and repeat.

From there, things will generally take over between the two of you on somewhat of an autopilot, in regards to making plans and what not. Either they will call you or you will call them, and the more times you go out on dates with one another, probably the frequency with which you see each other will increase. Remember, the whole idea of dating isn’t necessarily to fool around and have fun, but rather to get to know one another better so that you may both make a call on whether a relationship could possibly work between the two of you. If you wind up in high hopes of a relationship with this person, and affectionate or sexual activity comes in, I’d suggest at that point, try to show them at least a little commitment with fidelity, meaning no activity of either nature with other men, and possibly (entirely up to you, but sometimes helpful), stop dating others as well. By doing so, it is expressing to them that you are interested in taking things further than just a dating relationship, and highly decreases the chances they will walk away from you, the only exception being if they are into open relationships. If they are ready to progress into a serious relationship, they will strike at the advantage if they catch the hint. If not, if the both of you have been dating for a long period of time (several months to even years), chances are they may not even be ready within the next long period of time, and though I wouldn’t necessarily say resume sexual activity or anything like that with others, I would state to start dating around and exploring other options, being there is something that is obviously holding them back from fully committing to you. Just make sure before doing this that you did allocate them enough time, and were trying to move at a speed that should have been comfortable for the both of you.

That’s about all there is to getting back into the dating world and starting up a relationship. I do have one minor suggestion on another part of your submission which may help you. I understand that you and your ex are now best of friends, but if you find someone you really like and want to start a relationship with or even if you enter one with them, you need to be willing not to let your ex interfere in any way. Having a companion that sees or hangs out with their ex alone can be extremely uncomfortable for the opposite party in the relationship, and though I do think that trust is one of the biggest necessities to a relationship, there shouldn’t really be any moments in time where it is the only thing holding the relationship together, or rather where one partner needs to rely on their trust in order to stop them from leaving. I am by no means trying to tell you that you need to leave your ex and best friend behind, but rather stating if you are to be in a successful relationship, you need to compromise if your new companion is uncomfortable with you hanging with your ex… For instance, bringing your partner with you when you go to see your ex would be probably the best idea. All in all, I hope I answered your question effectively, and I bid you good luck in your future dating and relationships.

- Michael Pietrefesa

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Michael:

Thanks for your question. Let’s note that though you present as a gay man, your issues have little to do with sexual orientation. They are universal human concerns, so let’s simplify by treating them accordingly, focusing on your two main questions.

First, regarding not knowing how to date - join the club. Many of us feel this way, and it really isn’t about the nature of your first relationship. Dating is a basic social skill and some of us (most of us, actually) have less aptitude for it than select others. The good news is that when we humbly acknowledge this, then we can get on with developing those skills over time.

Because this is a common challenge, there are a zillion services aimed at this need, online and otherwise. Some purport to teach you social skills, while some are actual dating services, and everything in between. Take some time to talk to your friends and to consider whether such services might be a good investment for you.

Regarding what you want, I think you were right to use the expression “Holy Grail” and, as it conveys the notion of seeking the unattainable. Looking “out there” for something that doesn’t exist is an excellent way to set yourself up to suffer, so much so that a year from now you will bitterly grumble that “there are no good men out there.” We tend to cling tightly to our “wish list”, as if it were the answer, whereas actually it is the problem. We hold it up like a shield, and it gets in the way of our making genuine contact with others. We self-absorb on what we want, not seeing the irony that “self-absorption” is a quality we would reject in someone else, per our list!

If there is any perfection to be found, it will be in the form of your perfecting yourself by getting to know yourself better. How does one do that? Consider these possibilities:

*Let go not only of the notion of “Mr. Perfect”, but of a conventional “results-orientation” to dating. That is, rather than seeking an outcome, find your satisfaction in the PROCESS of dating. If you want to be as close to Mr. Perfect as you can be for your future partner, then refine yourself by dating with class and integrity. Have the intention to make genuine contact with each prospect; be kind to them and try to see value in them as they are. This is a vivid contrast to the wish list mentality which sets you up to find fault and judge others. I have seen many people with rigid wish lists who are still “on the market” 20 years later. They complain about the lack of good prospects, unable to see that THEY are the problem.

Dates seldom go the way we would want them to, so letting go of the attachment to a certain outcome can be a huge relief. Make your goal to “go with the flow”, accepting what comes up in each date and seeking a certain contentment with it, regardless of what the outcome will be.

*Realize that at your age, if I may say so, you probably don’t know what you really want. To the extent that you do, it will change. Generally, the people we end up attracted to don’t meet our list anyway, so just relax and FEEL what is right rather than muse about it too much. The self that does all the musing - “Let’s see, he should be tall; I prefer blonde, witty but not too chatty, etc” - that self wants to be satisfied but what really happens with time is that he gets demoted! We stop taking our ego chatter so seriously.

*Be careful with the commitment thing. I have seen this one as a straight man dating women: there is a certain demanding tone about “commitment” in the first five minutes of meeting. How could I be committed to you when I don’t even know you? True commitment is not something that can be mandated; it arises organically, with time. Remember, even if you found Mr. Perfect and he were committed, there is no guarantee that he won’t get hit by a truck tomorrow, so our inner security has to come from something else that the notion of our partner’s commitment.

So refrain from “screening prospects”, as if you were buying a dish washer or something. Relax and enjoy the process of being with others. If we cling to fantasies of certain results, then dating can be a royal pain in-the-butt. If we enjoy the process, if we make an adventure of it, then we are slowly perfecting ourselves so that when the right person comes along, we will be ready. I might finish by disclosing that I didn’t meet “the love of my life” until I was 42. Relax and enjoy, and you will suffer less than I did!

- Jim Ludwig

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