Hi Evan,

I am a 34 year old woman living in Canada. My first and only boyfriend six years ago pretended to be committed to me, used me for sex because he wanted to be with a virgin, and then he dumped me one month after taking my virginity. As a result of this awful relationship, I have some pretty major trust issues, and find it hard to accept the notion that a man might be genuinely interested in me.

About six months ago, I befriended an extremely good looking man in Puerto Rico through a flirting application on a social networking site. While he initially flirted quite a bit with me, I didn’t pursue anything since he had about a million female friends on his page, and that would make him out of my league.

For the majority of the time I’ve known him, we would chat occasionally, maybe play a game or two of chess online. However, about two weeks ago, things suddenly changed, and it seems that he is really pursuing me. We have both talked about wanting to pursue PhDs, and he talks about how we should attend the same university. Or, how he would like to “rent” a room from me if the job application I submitted to Ottawa comes through, since he could then study at the university in that city. And once I began taking a Spanish course, he has appeared online every night, under the guise to help me with my homework. One other thing, he has removed all his friends from his page as well as all of his own photos.

So the thing is, I don’t know what to make out of all this. What is going on with him? I am definitely attracted to this guy, physically, and intellectually, and I have sort of hinted to him that I think he’s a nice fellow and good-looking, but he never directly comes out and says he’s interested in me. But he hints around a lot, asked if I would ever consider moving to Florida or the Caribbean, and said I should visit Puerto Rico. Is he just being friendly? Is he just interested in helping me with Spanish and nothing more than platonic friendship? Or is there possibly more to it?

Renee

Dear Renee,

There’s ALWAYS something sexual underlying the motives of men. If you’re ever debating internally, “Why did he call me out of the blue?” or “Why did he offer me a ride home after work?” or “Why did he compliment my hair?” the answer is always that he wants to sleep with you.

Men and women can be friends if: a) he’s not remotely attracted to her, or b) he’s already hooked up with her and determined that he’s no longer interested.

This friend vs. more-than-friend concept has gotten a considerable amount of airplay, notably in “When Harry Met Sally”, wherein it was determined that men and women couldn’t be friends.

I have an addendum to that: Men and women can be friends if: a) he’s not remotely attracted to her, or b) he’s already hooked up with her and determined that he’s no longer interested. Without either of those conditions, it means that he’s physically attracted to her, the relationship has not been consummated, and therefore, there’s going to be sexual tension.

So even if you haven’t been actively flirting, Renee, after six months of emailing, there’s going to be, at least, a lingering curiosity. Our imaginations are fertile, and we can project whatever we want onto a stranger. Thank god for fantasies. But beware: it’s easy to confuse fantasy and reality. Your fantasy is that this sexy Puerto Rican guy will want to meet you for a hot fling in South Beach. The reality is that it sounds like he just wants to use you to get cheap room and board in Ottawa.

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I am a 33 year old single woman. I seem to always attract “great guys”, and we always have a lot of fun. But anytime I want to gently “clarify” what he wants (kids, family) nearly each and every guy I’ve dated shies away. I don’t think I come across as “easy”, and I am intelligent and take care of myself. However, I can never seem to transition properly from the “fun” woman to the “long-term” relationship woman, as the intelligent, loving partners I have had don’t seem comfortable ever talking about a future.

What can I do? I am so tired of feeling as though I am doing this all wrong in my attempts to find a real partner for the past 13 years. Your help is greatly appreciated as I am currently seeing another great guy. We’ve been seeing each other for just over a month now. He’s flown me to Bermuda to meet his parents, and I’ve also met his friends, who have apparently given me the “okay”. Meantime, I’m still going out with friends and about to go on two dates (that I really don’t want to go on but I’ve been told you’re supposed to “date”).

How can I broach the subject so my mind can be clear that he and I exclusive or not? Do I have to wait until he broaches the subject or can I? I am so tired of “games”, but I know it’s a game for the rest of my life even if I become a wife. Ugh.

Help and thank you in advance.

Robyn

I appreciate your sincerity and your desire to have a serious relationship. Your questions are among the most common questions that I get. Truly, what you’re going through is universal, and you’re not wrong to feel frustrated. Which is why I hope you don’t mind when I tell you to just take a deep breath and chill. All your answers will be revealed in due time.

First, a basic fact that you need to get, deep in your bones

Men reveal themselves in their efforts.

Nothing else they do matters.

Which is why you can have an incredible first date which doesn’t lead to a second date.

If he refuses to let you go, you have your husband. If he lets you leave, you have your freedom.

Or a best friend/fuck buddy who doesn’t want to make a commitment.

Or a two-year-relationship that doesn’t result in marriage.

In other words, he can be attracted to you, want to be in love, dream of having children, and yet be perfectly content biding his time with you for a year until he finds the woman he does want to marry. You may say he’s using you. Maybe. Maybe not. But as long as you’re both happy in the relationship, does it really matter?

I can almost hear you screaming, “Yes! Yes, it matters! I want to find love, my biological clock is ticking, I feel all this pressure, and I don’t want to waste my child-bearing years with some jackass who doesn’t know the meaning of ‘shit or get off the pot’!”

Very well, then. Leave him.

Voila. You have your answer.

If he refuses to let you go, you have your husband. If he lets you leave, you have your freedom.

This is far easier said than done, of course. You actually have to have the guts to leave a no-win situation, and many women do not. They’d rather stay in a safe dead-end relationship than be alone. Which is fair. But you can’t blame a guy when you turn 42 and he hasn’t proposed to you after 6 years. You can only blame yourself.

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Did you know that you can make other people more fun and interesting by asking them more fun and interesting questions?

What are some of the most interesting or fun questions you’ve asked that have elicited successful responses?

What are some of the most interesting or fun questions you’ve received from some of your matches?  Did you respond to these questions in a positive or negative way?

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Do you rely on people to write to you online? 

Or are you more pro-active about making contact? 

Do you have greater success by making the first contact or by waiting for potential matches to make the first contact?

What do you think of winks and icebreakers?  Do you ever use them or do you prefer an email as the initial communication?

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I dated online from 1997 until 2006. I went on over 300 dates in that time.

How long have you been looking for love online?

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Great usernames are usually puns or plays on words.

What’s the most memorable username you’ve ever seen on a dating site?  Was it memorable for a positive or negative reason? 

Are there certain elements of a username that make you steer clear of an individual?

What made you choose your username?  Was it a physical characteristic about yourself or a hobby or interest you have? 

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Do you know what a man expects out of a first date?

Have you ever bothered to ask him?

If you’re a female reader, please share some of the things you’ve done on first dates that you feel ensure a second date.

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How many times a year do you get set-up or get a number at a bar?

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