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Elliott, LPCC, NCC
Elliott, LPCC, NCC, Psychotherapist
Category: Relationship
Satisfied Customers: 7664
Experience:  35 years of experience as a Licensed Professional Clinical Counselor, National Certified Counselor and a college professor.
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I met a man through mutual work friends. We seemed to have

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I met a man through mutual work friends. We seemed to have an attraction and flirted a little over email and gchat. Three weeks ago I asked him out and he accepted enthusiastically. We went out and had a great time. He asked me lots and lots of questions about myself and soon we were holding hands and kissing. I told him I was a single Mom and 3 yrs older than him but he didnt seem phased. That night he texted me. Next night I texted him and three days later I gchatted him. All flirtatious and he was engaged but no mention of another date. I know he just started a new job and he went on vacation for a week (back a few days now). Do I take my cues and never contact him again? So tempted to reach out but don't want to appear desperate.
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Dear friend,

He is already interested in you. Perhaps you are a more suitable partner than his fiancee. You did hit it off quite well and seem to have a strong attraction.

There is a huge difference between being desperate and being very interested. There is no embarrassment in that.

Contact him. It might take a few times. You have much more to win than you do to lose. If you don't contact him then you have already lost.

He had a vacation break and may need to get reoriented. He is probably seeing the fiancee but that doesn't mean that you have fallen off the face of the earth.

I strongly urge you to give it a try. It may be the best gamble you ever took. If you don't win, you suffer a small disappointment.

I wish you great success and shall keep you in my prayers.

Warm regards,


Customer: replied 4 years ago.

By engaged I did not mean to be married. I meant that he was engaged in conversation! Although he did not initiate those next two texts/ gchats, he responded immediately and asked questions etc. My friends tell me - if a man is interested he will let you know. And they say since I initially asked him out, the ball is in his court. I am of two minds here. I have sent clear signals of interest that he has not pursued. Yet I am confused by his signals. Perhaps he strings me aling because it's good for his ego? I feel I have been direct - by contacting again, do I not appear desperate?

Dear friend,

I don't think so. He may just be a guy that isn't that socially adept. He did let you know in HIS way that he was interested and may not know that the ball is in his court. You are not desperate but you are interested.

You are very afraid of failure and are perhaps ready to make this an issue of not appearing desperate. Even if he thought that (which I doubt), then so what? If he is not interested then so be it..

One of my old friends used to say, "Nothing ventured, nothing gained."

It is really up to you.

I wish you courage and a strong spirit of adventure.

Warm regards,

Customer: replied 4 years ago.

I guess the question is: when do you give up then? One more email suggesting a drink? How much is too much? I should add that this man is extremely socially adept and may be what we women call a "player" - suucessful, handsome. I have seen the vacation photos and it's him and lots of women. This man can clealy have his pick and knows it. Does that alter your opinion?

Dear friend,

You saved that key information for last.

Handsome and succesful men can often have their pick of women.

However, they usually wind up picking one of them. You have plenty to offer. Its worth an email and an invite for a drink.

Your instincts are probably right, but you can invest a few electrons and send him a one-line suggestion for meeting for a drink.

Don't sell yourself short, ever.

Warm regards,

Elliott, LPCC, NCC and other Relationship Specialists are ready to help you

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