Rupert is a 36 years old man with a soft tissue disorder and is obviously out of shape. He writes, "I am trying my best to lose weight and I have made progress. I am attracted to younger, athletic women with hard bodies. Problem is: they're not attracted to me. I usually get more "Holla" from older, out-of-shape unhealthy women. I want to wait till I am fit and trim but I am lonely. My question is: Will I have to wait until I get to my goal weight before I am ready for a relationship? Or Should I settle for what and who is available even though I am trying to better my health standards in a mate?"

People look for similarities in their partners

I hope you realize this, but even though women might disagree and sometimes opposites attract, they are always looking for a long-term partner despite being in the dating game casually. Obviously, they try to target men that they find attractive and who will find them attractive. No wonder then that skinny people are attracted to and targeting skinny people.

There are two solutions to your dilemma.

• First, date casually whoever is available right now and be upfront and honest about it. Say that you are not looking for a serious relationship at this point. That will allow you to go on occasional dates and fight your loneliness.
  
• Secondly, date women in your situation that you are most likely to run into a gym. They are also trying to lose weight and become fit. That way you have something in common and eventually you both will have what you want. Yep, you can go out on a workout date.

In the meantime, you can work to get fit so that you can then target your dream girls. Unless you have something else that is incredibly appealing to women (e.g. money, yacht, beach home, unique talent, etc.) it will be hard to attract an athletic woman till you are not fit.

Shekhar in Calcutta, writes, "I want to say something about my initial flirt. In my flat I have a big window. I have been passing my time there only because I like cool ocean breeze and often enjoy a glass of wine there. One day I found a woman from the apartment in the next building looking at me. While I was watching she didn’t give that much of response. After two or three days I did the same. Then she started to shut the window. After a few weeks, she also tried to see me little bit. Now she is looking at me more often and it has been going on like that. One more thing, for the last two days she is also using my same time to go to her office and I could meet her on the way to the train station. So is this girl interested in me or what? Am I going the right way or not? Please help me."

How to find out if a neighbor is romantically interested?

It appears that this girl is definitely interested in you to some extent but I am not sure if this is going too far because both of you are way too shy.

I think the logical next step for you will be to casually approach her while you go to work and see if she is interested in you. Just go up to her and say hello and tell her that you are interested in friendship with her. If she calls the police, you should stay away from her; if she seems inclined to talk more about work, life, etc., you might end up finding out that she feels the same way you do.

Gilbert writes, "I like a married woman but I don't think she is interested. How do I find out. I just want to keep it casual, NSA. She is a really cool woman otherwise but I am afraid I will upset her if I tell her I want her."

As you said, she is not interested, but what makes you think so. Remember that many married women simply assume that no one will be interested in them (though vast majority of them are not interested because they are truly faithful). That means that you must make sure before assuming this that she is not interested and is not inclined to be persuaded either. So that you don't spoil your friendship with her and make a fool of yourself, please do not say anything directly or make a move. You have to watch her moves to see if she sees you as a "brother" or she gives out seductive signals.

Another way to test is to ask her hypothetical questions. For instance, if you are watching television and see Megan Fox, you could joke, "Gee I would give up anything in the world to spend a night with Megan Fox. I wouldn't care if I were married or if she were married. So who is your favorite man that you would do the same?" Keep it only as a joke. If she says that it is Wilmer Valderrama or whoever, you can guess that she is persuadable but if she comes out and scolds you for even asking that question or says that she will never do it because she is committed to her husband, you will know that you low probability of convincing her.

Making a married woman have a no-strings-attached relationship is no easy task if she is not the one to suggest it, but the #1 thing that makes it happen is complete trust in the man. She must know in her heart that you are a man that can be trusted so gain it. Do not gossip with her (it will make you come across as a man who likes to share secrets) and be there for him when she needs you.

Allison writes, "I have had this friend for about 4 years and we have gone through some ups and downs due to each others romantic relationships. We clicked right off the bat and became very close very quickly. I always had a little crush for him, but I respected our friendship too much to profess any feelings. I got into a relationship about 7 months into our friendship and I feel he felt neglected in some way. He ended up moving to a different state to finish his degree and we only talk once in a while and see each other once or twice a year. I am currently in a three and a half year relationship (it has been long distance for the past 7 months) that is currently having problems and this very day we are "on a break" so we can think things over on our own terms. This past weekend, this male friend was in town and we had a great night together. I had lots of fun and maybe a little too much to drink. We almost crossed the line several times, but I held back because I am in a relationship (he is not). The next morning, we cuddled and were very affectionate. Since that day (4 days ago) I have just been smiling and happy, not sure if I am falling in love with him all over again or just glad to see him. I am also bothered because how can I have feelings for someone else and be in a healthy relationship? Anyways...what do you think? My friend and I have always been pretty affectionate when we hang out, and maybe he is just like that."

Liking a best friend

Well, first of all, it is not unnatural to start liking your best friend or even falling in love. In any case, you were attracted to him early on, so it was even easier to fall for him.

Retaliation relationship

Secondly, now that you are single, and coming out of a possible breakup (on a break usually is not a good sign), you are feeling vulnerable and lonely, and that is why the idea of a man who has been solidly behind you all these years and who you can trust so much, is so appealing. Of course, this is also a likable, happy man that you are so close to. That is why you don't feel any guilt and are enjoying his and your feelings for each other. Yes, you are technically in a relationship, but the way you describe to me, it is a dysfunctional relationship and if you do not end it sooner or later, it does not have a very bright future.

What I would advise is that you spend as much time as possible with your friend and keep monitoring your feelings for him, and of course, his reaction. If you are hitting it off and realize that he too is romantically inclined towards you, it might be time to have a serious chat with him to see if you want to pursue a relationship. At that point you can breakup with your current boyfriend.

I think you should use all the tricks that you would for a girl your age but there are a few differences with respect to mature women:

1. They may not necessarily be interested in dating, particularly if they are already in a relationship.
2. Many find it difficult to believe that a younger guy may be interested in them, or at least, be serious about them.
3. Some have low self-esteem due to aging and often wrongly believe that just because they have stretch marks or sagging body, younger men would not find them attractive.
4. They also suspect that you are interested only in sex and are not serious about emotional involvement.
   

If you are able to address these issues, you will be in pretty good shape.

Oscar writes, "I am in college and have noticed two girls in class sometimes smile and laugh when they look at me. Sometimes when I make a comment in class they laugh. I know that some girls like to have fun. I do not want to misread people or take things seriously. How should I view their behavior?"

Yes, in 90% of cases this is a good sign, especially if the laugh is as if they are a little embarrassed, shy, playful, naughty, etc. and also exhibit other body language signs of interest and flirting. I am guessing that one of them is teasing the other about you or they both tease each other about you.

The only remote possibility that you need to eliminate is that these are not mean girls that are actually making fun of you for some reason.

So try to talk to them casually about something class-related and if they are warm and pleasant, I think it is a good idea to move forward to find which one of the two is actually interested in you.

Sita writes, "Is it true that generally Japanese boys tend to dislike British-Asians [British born and parents from a South-Asian country]. I know every boy is different but in general. Would they even date Brit-Asians? Because my friend also told me that they're only interested in Caucasian people and would only date them."

In my numerous conversations with Japanese people they do have some reluctance to date South Asians and other dark skinned people but not all people are alike. I have actually known people (not British) from India/Pakistani/Bangladesh date and marry Japanese.

So if you are otherwise interesting give it a shot. I know a lot of them travel to Britain and some even study English there. Start to find out how you can sort of give some English lessons to them and get to know the group (they stay in groups actually) and the next thing you know you might even find a boy that likes you.

Stay in touch and let me know how things turn out and what help you need.

Nick writes, "I want to date a cougar, what do I have to do to get a mature woman?"

For those of you who are wondering if Nick likes dating animals, a cougar or a sugar mama is a word used to describe a lady who likes younger men. Think Demi Moore.

I always like to tell my readers that a hunter should go where the prey is. If you want to fish, you don't go to the mall, you go the sea or a lake.

So if you are interested in dating cougars, you have to explore places where mature women might hang out. So if you have a job in the mall, you do not want to work at Abercombie & Fitch but working at Talbots or Chico's or Macy's is worth it. You get the idea.

How to identify who could be a cougar?

A cougar typically takes good care of herself and dresses trendier. She will dress more like someone who is 10-15 years younger than her. I have seen that many of them are in much better physical shape than their peers, though, this is not universal (considering how fat people are these days in general). She also is more aware of what is popular among young people and rarely talks about issues that interest women of their age (so you really wouldn't have to learn about parenting or retirement savings).

In addition, once you find your prey, treat her like you would someone your age, so that the age difference does not come as an issue between the two of you. You will need to woo her the way you would woo a girl your age.

And finally, never dwell on the age issue even if she does. Tell her that it is the person you care for rather than the age. Then, immediately change the topic.

Courtney writes, "I met someone for the first time. I have never had anyone make me feel this way and there was no intercourse involved. I feel that he felt the same way about me too. What do I do? He is a Hollywood celebrity. He has my number and I have his. I want him so bad."

If he felt the same way (as you tell me) and if he has your number, you should just wait for him to call you back. That would be the right thing for a gentleman to do.

Having said that, do not keep your hopes too high. Depending on how big a celebrity he is (and I am assuming that you are not a celebrity yet), girls probably come on to him all the time and he might not remember much about them later on.

But remember that George Clooney dated a waitress and Leonard DiCaprio married a bartender. In other words, celebs date and marry non-celebs all the time.

In any case, if you still want to give it a shot, wait for a week or so. Research about an activity that might interest him (based on what you know about him) -- it could be an art exhibition or restaurant or movie -- and give him a call to say that you plan to go and were wondering if he had some time to hang out with you.

If he completely ignores you or does not even remember meeting you, then it means that he was yet another Hollywood star who takes dating rather casually.

Cynthia writes, "I started hooking up with a younger guy (who pursued me) who has a girlfriend. For me it is just fun, but seems from little comments, that he seems to have a problem with the age gap and situation. I broke it off because I cannot have fun with someone who is uncomfortable. My friend thinks he is really open. How can I tell what the real problem is?"

The best way to do it is to find out from him.

If he pursued you despite his not being single, he definitely has some has interest in you, and the age is probably not a major issue. We all have some level of discomfort in every dating situation, whether it is the age, race, ethnicity, education level, distance from the town, etc., and if the person is otherwise good, we all make compromises.

So go with an open mind and hint to him that you are interested in exploring a relationship with him. If you find out through his behavior and conversation that he is still biased about your age, time to say goodbye.

But you might very well find out that after he learns more about you, he might feel more comfortable with the idea of dating someone older than him.

Pedro, a Hispanic-American, writes, "I met my girlfriend online, and we have been communicating almost everyday since we met 6 months ago. We love each other dearly and plan to marry eventually, even though we haven't "physically" met yet. We are going to meet in a couple of months (I'm traveling to Brazil). There is only one thing that I'm worried about. I'm 51 and she's 32 -- big age difference, and although she says that the age difference doesn't matter, I am still worried a little bit. Her father is Chinese and I am worried that she will have many problems with her family once she announces that she's in love with an older Mexican-American guy. We plan on her coming to the USA to marry me, but in the mean time, I need to know how to deal with her family -- an Asian family that has been established in Brazil for many years."

Marriage for green card

Not that I suspect that with your girlfriend, but I hope that you realize that many women simply want to marry anyone with an American passport -- the so-called marriage for a green card. It is something that you need to think about and watch out for. If she shows desperation then you need to really make sure that she won't marry you and then leave once she gets her green card.

Marriage through online dating without a real date

While I am a big supporter of online dating, I am always suspicious of people falling in love and planning to get married without ever meeting. Buddy, if you want to listen to my advice, slow down. Yes you can do both but make sure that you are even talking to the same person behind the webcam or email. I have heard enough stories from my readers who found otherwise once they met -- people lie a lot more than acceptable while dating on the Internet. That is why I suggest that people go a little slow in online dating.

How to tell your family about your foreign boyfriend who is also older and of a different race?

Do I understand it right that she has not yet told her parents that she is dating you? You better make sure that she does so right away and if her parents have a huge problem with that and she wants to listen to them, then you better not waste your time and money traveling to Brazil. This is an issue that she needs to handle. You need to strategize with her but she is the one who knows her family better than anyone else. She is the one who has to tell them that you are a wonderful guy, that she is in love with you, and that they should join her in happiness. Of course, you will need to formally ask for her hand in marriage, but I think that you may be trying to do too much in your first visit. I would suggest that you spend this trip on getting to know her better and dealing with issues I have raised here. Come back to the US, think things over, make sure that you are comfortable with everything, and then actually make another trip to ask for her hand in marriage.

Remember that I wish you well and have nothing against you or your girlfriend -- I raised a few questions so that you get an unbiased opinion from someone before you take such an important step.

You know the term "sugar daddy." He is a wealthy, older man who uses his money to hang out (or even marry) drop dead gorgeous, but younger girls.

Do you know the term "cougar?" She is an older woman who dates younger guys. She may or may not be rich.

So combine a sugar daddy with a cougar and you get a sugar mama. She is basically looking for her boy toy either because men her age are already married or are divorced with children with all kinds of issues that they have paying for child support and the mid life crisis that often turns them into cynics. These women want no drama, just studs to have a good time.

So how can you get one of them?

I spoke to a few women like that and they all mentioned good physique as their #1 requirement. They also do not have much need for men in sneakers and baseball caps who look more like the men that deliver their laundry. They want men that literally step out of a GQ magazine. You don't need to have the money, but you better be interesting, have a sense of humor, and have no attitude.

Mark, a 26-year old, lives and operates a business in Puerto Rico and has found instant attraction towards an 18-year old local Latina. "We have been dating (if you are single, try our free dating website) for only 2 weeks, but I have liked her since the moment my eyes saw her, and I am 99.9% sure that the feeling is mutual. I am ready to tell her how I feel about her. There are a lot of gringos here, and a lot of them come here for a few months and leave. Should I tell her that I am here for the long run and Puerto Rico is my home, and I am not going anywhere. Or should I just leave that out until later. Would you recommend I just follow my heart with this?" he asks.

It will be nice to hint about your long-term plan by talking about your business, the fact that you own it, and how you would love to spend the rest of your life in this beautiful island growing your business. I think considering that you are not a tourist, she knows that you are there long term.

Since you have been dating for just two weeks, I would say that you want to keep it subtle and only give hints at this stage rather than say "I like you so much I can marry you now." You know what I mean. Emphasize that you enjoy her company and would love to spend more time together with her. Then wait for her to respond. This should be more than enough for this date. As you get to know each other more, you can be more open about your emotions.

Rules of engagement for relationship with military men

Relationship with miltary men/women is not easy. You never know when they may have to answer the call of duty. Of course, all men and women who love these people need to be supported, but sometimes a breakup makes sense so that others can move on with their lives.

Dave and Jenna are such a couple who decided to take a break from their relationship so that he could go and serve his country. They have been together for four years and he has a commitment to serve in the armed forces for four years. "While I am doubtful it will work out when I am back, but Jenna is convinced we will be back together. She has made it clear that while we are apart we will continue dating but will make no commitments. What are some suggestions you would offer to help ease the heartbreak while I'm off bettering myself and our country?" he asks.

You both deserve my congratulations for taking such a mature attitude towards your relationship. As you both understand, four years is a very long time and a lot can change. What I do not like about your agreement is that you will make no commitments to others who you will be dating. Isn't it unfair to them that you will be "using" them in some way?

If you date, then be ready to commit

If you two are so committed to each other that you will not commit to anyone else, then you should not breakup and have a long-distance relationship. On the other hand, if you wish to date other people, you should date as if this relationship is over. And at the end of four years, when you return, if both of you are still single and interested in purusing a relationship, then you should talk about it.

However, if you still want to pursue the agreement that you both have, then in all fairness to the people you may be dating, you should be up front about your situation. Tell them that you are clearly not looking for a serious relationship, just casually dating without commitment, because you do have someone special in your life.

Also, insofar as both of you are concerned, make sure that you both stay in touch through email, letters, phone, etc. on a regular basis to the extent possible.