Is Having Sex on a First Date a Good Idea?

When it comes to dating and hook-ups, there's no question that sex is a lot more easily obtainable for gay men than for straight men, even at a first meeting.

So, the question then becomes, is it a good idea to have sex on a first date?

The answer is, like for most questions in life, "it depends".

The really important question to ask before you consider having sex on a first date is whether you consider the guy you're meeting to be a prospective romance.

If after the first date, you don't consider the guy to be a strong romantic prospect, but you still feel physical attraction to him and you're, ahem, horny...having sex with him, assuming he's agreeable, is really not a major issue. I'm not one of those prudish aunty types who will tell you that casual sex is to be frowned upon. In such an instance, your date has morphed into a potential hook-up, and it's only a question of whether you want to proceed all the way or you're just not in the mood. Either way, there are no major consequences (assuming you practice safe sex).

The dilemma arises when the chemistry between you and your date is so strong that both of you feel that the date should culminate in a night of passion.

Some people will say that there's no better way to cap a great date than to end it between the sheets. And indeed, there's nothing quite like instant gratification. However, my advice is to hold off on the sex on the first date.

[I am fully aware that there will be people who will disagree with me, and that's fine too. Advice is just advice, and its utility may be highly situational.]

I've never really bought the whole BS about how having sex on a first date can compromise your development as a couple, and how it may negatively affect commitment from the other guy as your relationship progresses. If the guy is a player or commitment-phobic, that will be a problem no matter whether you sleep with him on a first date or not.

No, the main reason why I advise against having sex on a first date is because it robs the two of you of much greater satisfaction later in the relationship when you do have sex for the first time.

Assuming the two of you enjoy such great chemistry that the first date has a serious shot at progressing to a far more significant relationship, it's a given that the sex will happen. It's only a matter of time. But the benefit of holding off on the first date is that when you do have sex with the guy, the two of you will know each other better, have a higher comfort level with each other, and are more likely to be good, giving and game to each other. Oh, and there will be a lot more cuddling before and after, which many people enjoy just as much as the sex. All that translates into much more satisfying sex the first time.

If you're not convinced, think about the very first time you had sex. Was it good? If you're like most people, the very first time you had sex was most likely NOT good. At least by the standards of what you consider good sex now. And by sex, I mean with someone else, both of you naked, doing the full ensemble of acts and positions. Quickie handjobs and blowjobs do not count.

Most memories of first experiences with sex are marked by self-consciousness, hesitancy conflicting with heavy desire, performance anxiety, and just plain old fumbling with the mechanics of sex.

We all become better at sex with practice, but unless you're the type that has, ahem, a lot of experience, it's not uncommon to have a few miscues or awkward moments when having sex with someone new for the first time. A smooth synchronized performance it usually is not. And even if you are very experienced, the other guy may not be.

So, given the possibility of awkward moments AND the fact that this guy that you feel so strongly attracted to but barely know could be THE ONE, why have sex on a first date when there's just so much more at stake and so much more pressure to have great sex? If the sex doesn't turn out so well, then what? The subpar experience could have been due to purely situational reasons, but one or the two of you might decide to throw in the towel and not proceed further, which might be a great pity.

Why not wait until you get to know each other a little better, then if the awkward self-conscious moments do arise during intimacy, the two of you can laugh over it and be good, giving and game to each other in bed because the two of you are already so comfortable together. The experience will have as much passion as first date sex thanks to the anticipation, but will be much sweeter due to the closer emotional bond.

Of course, I don't advise holding out on sex until the two of you have had many, many dates either. Assessing sexual compatibility is an important consideration too if the relationship is to progress. Having great sex the first time with someone new is really just a matter of the comfort level. It's just that it's highly unlikely that you can achieve an optimal comfort level on a first date.

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7 Steps to Being Relationship Ready

It's hard enough being gay. But dating when you're a gay man is even harder. So, what are some things you can do on your end that make it easier for you to be in a healthy, committed relationship? Here are 7 steps to being relationship ready:


1. You need to be in a healthy relationship with yourself before starting one with someone else.

To be in a healthy relationship, you need to first be comfortable in your own skin. There should not be feelings of guilt or shame for being gay. Instead, there should be a quiet confidence in your own self-worth.

Self-knowledge is the most important kind of knowledge. And for most people, it is not an end state, but a continuing journey. We each of us grow and change with the passage of time, and it's important to love the you that is you.. As Carrie Bradshaw said in Sex and the City, "the most exciting, challenging and significant relationship of all is the one you have with yourself."

Not everything in your life has to go swimmingly before you start dating seriously, but you should have some idea of how you want your life to unfold. You need not necessarily have any concrete plans per se, but you might want to evaluate your existing relationships with the people important in your life, or your career perhaps, or your values, your priorities, or any combination of the above.

Finally, it is important to retain your identity as an individual even when you are in a relationship. As the sex therapist Esther Perel speaks about in her TED talk, the modern committed relationship is a contradiction; we have to reconcile our fundamental need for security, comfort and permanence from our partners, against the opposite fundamental need for surprise, mystery and novelty. It is only when we retain our identities as individuals that we preserve that erotic space which is so important for sustaining long term committed relationships.


2. You don't necessarily have to come out, but it certainly helps...a lot.

We talked about this previously in another post. Read it here.


3. Step outside your comfort zone.

The confidence that you will gain from setting a challenging goal for yourself, surmounting obstacles and finally achieving what you set out to do will help immeasurably, both in dating and in all other aspects of your life where you must risk something to get something.

Dating and relationships are about putting yourself out there; they are as much about risk-taking as anything because you risk rejection, disappointment and heartbreak when you expose your heart.

Forcing yourself to step outside your comfort zone will challenge preconceptions you had about yourself, allow you to gain new self-knowledge, and bolster your self-confidence. This new-found self-confidence will sustain you when you encounter the inevitable rejections and disappointments that are part and parcel of dating and relationships.

Some examples of how you can step outside your comfort zone and challenge yourself:

1. Finish a marathon.
2. Take up an extreme sport.
3. Volunteer for a community organization.
4. Learn a new skill.
5. Start a personal project that requires dedication and commitment.

Do any or all of them. Or come up with your own. They are all eminently possible for an ordinary person to accomplish. I can attest to that. Creating 7for7 is the fifth one on that list for me.


4. Invest in yourself.

It is much easier to attract someone worthwhile to be in a relationship with if you yourself are attractive.

Attractiveness is not solely physical. If you don't have the looks, work on your body. If you have neither the looks or the body, rely on your charm, your personality, your wit. The good news is that each of these aspects of attractiveness can be improved.

In general, the male body only looks good when it is muscled. While some guys are blessed with better genetics, it is a biological fact that muscle is the most adaptable of tissues. It is both a curse and a blessing that for a man to look good, he needs to exercise. A curse because there are no gains without effort, a blessing because it is entirely democratic and equitable; everyone has to exercise and one gets rewarded based on exactly what one puts in.

This doesn't mean that every gay man should live at the gym. Neither does getting a good body necessarily entail going to the gym. It does mean eating sensibly, incorporating regular physical activity, such as sports, into your lifestyle, and having reasonable expectations, both of yourself and others.

As for the aspects of attractiveness that are not skin-deep, these can be cultivated as well. Read widely. Think. Develop ideas and opinions. Have a point of view. Learn new skills. Practice the art of good conversation. Be interesting, because that will hold the attention of potential mates long after your looks and body have faded.


5. Prioritize what you're looking for in a relationship.

Part of the process of dating is figuring out what's important to you in a relationship and what are things that are negotiable and just nice-to-haves. The physical aspects are important, but it's not helpful to have impossible standards, especially if you yourself can't meet those standards.

Avoid the checklist mentality. It's not about trying to avoid being picky. Being picky is good. Rather, be picky about the right things.


6. Don't wait for the right guy to appear in front of you. Create opportunities for yourself. Make things happen.

Too many single people, straight or gay, bemoan that there are no good guys/girls out there.

Waiting for something to happen when you "least expect it", relying on serendipity to deliver the guy of your dreams to you...these are not reality-based ideas. In short, simply hoping is not a viable strategy.

If you're going to find someone, you have to put yourself out there. Speed dating, online dating, asking friends for introductions, participating in activities and events, these are all ways to increase your chances of meeting someone worthwhile.


7. Be prepared to work at any relationship you get into.

Relationships are hard work. Don't expect that you and the guy you're dating are an item after just a handful of dates. The two of you will have to put in the hard work of getting to know each other beyond just the initial phase of attraction.

Even if the two of you have established a certain level of comfort with each other, it takes a long time for love and intimacy to develop beyond the initial flush of passion. And that takes commitment, solid communication, compromises, empathy and a shared sense of destiny.

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Can a Guy be Closeted and Still Be in a Successful Relationship?

Short answer: Yes, but the likelihood of success is much lower.

Long answer:

Let's start by defining what it means to be out of the closet. There are varying degrees of being out of the closet. At the risk of oversimplification, the degrees of being out are, in increasing order of "outness":

1. Out to yourself;
2. Out to other gay people;
3. Out to straight friends and other people you take a risk being rejected by, but whom you can ultimately cut out of your life if need be;
4. Out to family, colleagues and other people you still have to interact with whether you face rejection or not;
5. Out to the general public.

Where you are at in the stages above matters. Very simply, the further you are along in being out, the more likely it is that you will be in a successful relationship.

Someone who is not even out to himself (stage 1), i.e. he is still in denial or unsure about his orientation; such a person is not in any shape or form ready for a relationship, straight OR gay. Clearly, someone in that situation has deep existential and identity issues that they need to work out before they can embark on a healthy relationship with someone else.

It's not possible to start a relationship without dating first, and dating requires a person to meet other gay people, so by definition, someone who is actively looking for a relationship would be at stage 2. Just about everyone who is reading this post right now would be at stage 2 at least. But there's a big difference between someone who is at stage 4 and someone who is only at stage 2 in terms of how relationship ready they are.

[Stage 5 is irrelevant for most people unless you are a public personality, e.g. the former politician Vincent Wijeysingha.]


"To love at all is to be vulnerable." - C.S. Lewis

The reason why being out matters to the health of your romantic relationships is because being in a relationship is about being emotionally available to your partner, and also being vulnerable to your partner on emotional terms. It is not possible to feel deeply for someone without exposing yourself to being hurt by that person.

It is possible to be in a relationship despite only being at stage 2 above, but the benefit of being further along in being out is that it lends a sense of greater authenticity to all of one's relationships, whether those relationships are with friends, family or colleagues. That greater authenticity in turn makes it easier to open oneself up to intimacy with a partner.

Gay people growing up in a environment hostile to their sexual orientation frequently develop preternatural instincts in shielding themselves from emotional contact with those they are unsure of acceptance from. That includes family and friends. Without being out to one's family for instance, a gay person, on some subconscious or conscious level, might fear that their family's love and concern for them is purely conditional on them being straight and "normal". That fear of being hurt creates emotional distance between the gay person and the people who are closest and most important to him.

If that emotional distance was to be confined to just being between a gay person and the people he was not out to, it would not be such a great problem. But the problem is that the emotional distance oftentimes carries over to all of a gay person's relationships, diminishing the quality of friendships, closeness to family, collegiality at work and yes, emotional intimacy with one's partner.

Someone who is only at stage 2 is more likely to be emotionally guarded and hence less available emotionally to their partner. That makes it harder for a relationship to progress. As Woody Allen once quipped, a relationship is like a shark, it has to constantly move forward or it dies.


Second Order Effects

A second reason why being out helps make a romantic relationship stronger is that it places considerably less stress on a relationship, particularly if between the two people in a relationship, one is further along in being out than the other.

Someone who is not out is constantly censoring his answers to questions like, "How was your weekend?", or finds it impossible to share a large part of his life with other people. He may feel compelled to play the pronoun game, or simply avoid any mention of his personal life at work.

He may also feel uncomfortable appearing too close in public with his partner, or live in fear of being seen with his partner by his family or friends he's not out to. All these "second order" effects can place a budding relationship under considerable stress when the partner who is more out may resent how the less out partner is forcing him into intolerable situations.


Being in a gay relationship is hard enough, what with the lack of positive role models and societal acceptance, and how men in general, gay or straight, are not socialized to negotiate intimacy and emotions from a young age. A closeted man can still be in a successful relationship, but it will certainly be much harder and require more understanding and communication between the two guys in the relationship.

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Register with us at http://7for7speeddating.blogspot.sg/p/register-with.html

Post-Event Publicity 16 April 2014

7for7 just held an event on 16 April and the event was a success! Thanks to all the participants who attended and Elvin who graciously offered us his bar to hold the event.

The event was held at Out Bar on a Wednesday night, so while Out's normal clientele were around, the venue was quiet enough to permit conversation between participants.

Here are the event statistics.

Half of the participants this time round found matches.

Interestingly enough, one pair of participants matched up even though they already knew each other and came to the event together! They both indicated they didn't want to date each other, but at the end of the event, they both put each other down as a match.

Turns out that 7for7 events are a great place to test if you can move from the "friend zone" to something perhaps a little more intimate, without exposing your interest unnecessarily.

On a scale of 0 to 4, the feedback score was 3.4, highly positive feedback.

Some participants commented on the dim lighting. However, the venue being a bar, I hope participants can understand that the lighting is bound to be softer. On the plus side, soft diffused lighting hides the flaws in everyone's skin tone!

As for the space issues some participants mentioned, we are somewhat constrained by the fact that the venue must remain open to business, since the event is relatively small-scale and we cannot possibly reserve the entire space. We hope participants understand these constraints.

As mentioned during the event, we'll hold our next event when there is sufficient interest forthcoming. Till then, enjoy your matches for those who have them, and we look forward to seeing you again in the future.

Details for the Event on 16 April 2014

By now, participants who have registered for the event and confirmed their registration through payment should have received the details for the event via email. Also, the pre-event form has been released.

Please check your email if you are participating in the event on 16 April. We look forward to seeing you there!

What to Expect at an Event

Most participants at a 7for7 event would not have attended any kind of speed dating event before. Here’s what to expect, and some do’s and don’ts:

1. It is not a good idea to arrive late.

There are three reasons why it is not a good idea to arrive late. The first reason is that latecomers force me, as the organizer, to call them on their phones to check if they are coming. No-shows require me to carry out some last minute reconfiguration of the seating arrangements, which can be messy. To avoid this, I need to know if a participant is unable to attend the event or is genuinely late. Of course, if you are late enough, we will start the event without you.

The second reason is that arriving late can be like stepping into a lecture theatre when everyone is already seated. It makes for an awkward entrance, especially if you are alone.

The third reason of course, is that it may result in a bad impression on other participants who care about punctuality.

2. Arriving early is OK if you don’t mind socializing with the other participants.

However, if you are the reserved sort and inclined to sit in a corner with your phone, it is probably better not to arrive too early. As the facilitator of the event, one of the things I try to do is to strike up a conversation with participants who arrive early to make them feel more comfortable. However, I can generally speak to only one or two people at a time, and when other participants start arriving, I will be too busy registering them.

3. Dress well (but not in anything formal) to create a good impression.

Office wear is about as formal as it gets. It’s what I wear myself when I hold an event since I come straight from work.

4. If you feel awkward, shy or just plain out-of-place at the start of the event, don’t worry. That feeling fades quickly.

The comfort level of participants at an event noticeably increases after perhaps 20 minutes (about three speed dates), even if they arrived alone without knowing anyone. The reason for this is simple. Each speed date generally starts with the same few questions. “What is your name?”, “what do you do?”, “what are your interests?”, “what kinds of activities do you enjoy?”.

By the third speed date, the rhythm of the conversation becomes very familiar, expected, even a bit unexciting, which is why we limit the number of speed dates to only seven. The good part of this however, is that participants no longer feel awkward once the ice is broken.

If you are hesitant about registering for our upcoming event because you are apprehensive about how uncomfortable it might feel, this is a good reason why you should attend, because from experience, we know that those uncomfortable feelings don’t last and that participants generally enjoy meeting new people at the event.

5. At the end of each speed date, end the conversation smoothly and thank your date.

Needless to say, this makes the experience more positive for everyone and leaves a favorable impression.

6. After the speed dating portion of the event, mingle!

For many participants, this is really the best part of the event. The awkwardness of meeting random strangers is gone, the slightly artificial feel of speed dating is over, and yet, you have a mix of guys you have already introduced yourself to and with whom you can continue to deepen the conversation.

At the previous event I organized, I could tell from the body language of two guys who continued talking to each other after their speed date was over that there was chemistry between the two of them. And indeed, at the end of the evening, there was in fact a match between the two of them.

Or if you’re still up to it, you can get to know the other guys whom you did not get to meet.

And you know what? In the unlikely event you still feel shy, the seating arrangements guarantee that you already know someone at the event who has spoken to the other guys you have not met. So, it is not difficult to draw someone you’re attracted to but did not get to meet into a 3 or 4-way conversation.

7. Mingling is an art. So, take the opportunity to practice.

Anyone who regularly networks at professional events such as seminars and conferences already knows these things, but if you don’t, here are a few tips.

Make eye contact with the person you wish to talk to. Take the initiative and walk over. Listen with interest to what they say. Be an active participant in the conversation. Avoid monosyllabic “yes-no” answers, and when you yourself ask questions, ask open-ended ones that invite a more verbose response.

For example, if you know someone who works in sales, don’t ask “Are you in a client-facing role?”, which invites merely a yes or no response. Instead, ask “What kinds of clients do you work with in your job?”, which encourages the person to explain in a more detailed response. Questions like these make a conversation flow more naturally.

And if you need to disengage from a conversation, perhaps because you want the chance to talk to everyone at the event, do so smoothly. For example, excuse yourself to go to the toilet, or to refresh your drink at the bar.

So, there you have it. 7 tips for what to expect and do at a 7for7 event. We look forward to seeing you on 16 April!

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Register for our upcoming event on 16 April here.

Making the Most of a Speed Dating Event

The first 7for7 event was held in January this year, and from observing participants at that event, it's clear that there are certain things participants can do to make their experience a more positive one.

It's important to note that 7for7 is not a matchmaker. Our role is an event organizer and facilitator. Hence, it's up to participants to make the most out of attending an event. But don't worry. By reading the tips we list below, you're well on your way to having a great experience!

1. The laws of attraction are not suspended simply because you have 7 guaranteed dates.

What does this mean? It means you should take just as much care with your appearance as if you were meeting an exciting new guy for the first time.

Get a haircut. Dress well. Think about how best to describe yourself in just a few minutes. Make a conscious effort to be friendly and approachable at the event despite a long day at work.

2. At the event, you should be looking for that ineffable quality - chemistry.

Some participants approach speed dating as they would online dating. They come with a checklist and expect to meet guys who tick all the right boxes. And when they don't, they go home disappointed and decide that speed dating doesn't "work".

As an event organizer, my advice to participants is to keep an open mind when attending an event. Allow the conversation with each date to proceed naturally, and when your 7 minutes are up, think about whether if you had the chance, you would want to continue the conversation with that person.

Of course everyone has certain qualities they look for in a potential significant other, but the goal of speed dating shouldn't be to screen out the guys you meet based on your checklist. In fact, quite often, people are terrible at figuring out what's really important for them in a relationship and what's just nice to have.

Instead, consider the rapport that you build with your dates and think about whether you felt a connection and whether you would like to know him better. If you did feel the connection, put that guy's name down as a match on your program sheet. You can always decide later whether that was just a phantom feeling or something more substantial.

Which brings me to the next point...

3. You are not there at the event to look for a boyfriend / soulmate.

It's unrealistic to expect to find an instant hot new boyfriend after attending an event.

A match at a speed dating event is simply an opportunity to meet the guy you felt a mutual connection with, in the future in a different context, and to see if something more will develop.

Don't make the mistake of projecting too much significance onto a match. Overeagerness can be very unattractive on meetings following a speed date.

4. 7for7 arranges 7 dates for you at each event. But there will be at least 6 other guys that you haven't met following the speed dates.

Some guys leave right after the speed dating portion of an event. Sometimes, this can't be helped if you have a prior engagement.

But if you're free after the speed dating, mingle! You should be doing at least one of two things:

• Starting a conversation with the other guys you have not met; and/or 
• Deepening the conversation with the guys you have already speed dated and found yourself attracted to.

The goal should be to increase your interactions with other participants so you come away from the event with a richer experience.

And of course, what works well at the end of the event works just as well at the start. If you are early to arrive, take the opportunity to chat to the other early participants before the event starts.

A 7for7 speed dating event is ultimately what you make of it. As an event organizer, I can only do so much. So, take the initiative, put yourself out there and meet the guys. One of them could become something more than just a random acquaintance!

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Register for our upcoming event on 16 April here.