General Dating Questions/She's free now!


QUESTION: I have known this 25 yr old woman for about 1 1/2 yrs. I am 38 years old.
We were coworkers but she was sent to a different location 8 months ago. At first I thought she was scared of me but we eventually became friends. Ironically, we have communicated a lot more ever since she left. We text each other frequently.

When I met her, she was involved in a long term relationship. She has been 4 years with her boyfriend, but recently her relationship has gone sour because she wants to marry and apparently he has lost interest. She says she feels she has invested in that relationship for nothing.

We have gone out for drinks but only if a common friend is present. I've tried to ask her if we can go alone but she hasn't accepted yet. Our common friend has hinted she knows I like that girl, but... she also thinks that I like her.

Now... I've noticed that we always sit together. She touches me with her fingers, occasionally pats me, and often our legs touch. We see each other often at the gym, where I've noticed that she likes to step on the legs of the machines I work out on which, incidentally, are typically between my legs. Last Saturday, unless she didn't notice or think about what she was doing, she oddly wiped off her sweat with her t-shirt and basically flashed me. She likes to read 50 Shades of Grey and has asked me if it's true that I actually own s&m paraphernalia.

Beyond that, she typically comes across as a fairly innocent, inexperienced and somewhat religious person.
This week we will attend several workshops together (we actually shared our schedules and signed up for the same sessions). She is also attending graduate school at the present time.
I would like to utilize this opportunity to ask her out one more time. In the meantime, I suppose we will probably go to lunch together at least once this week.
I do think she is a keeper. But I really don't know if I can ask her how her relationship is going (our common friend told her in front of me that I'm just waiting for a chance to hit on her). Also, I'm curious to see if all the aforementioned behaviors mean something. Can this work out?
Finally, is almost 14 years too much of an age difference, even if I look younger than 38 and she looks slightly older than 25?

ANSWER: i wouldn't worry as to the age thing; under the circumstances, you have to just hang in there as you are doing, essentially as  a friend, until she ever splits up with the guy...all the flirtation stuff really doesn't mean alot--the bottom line is in her mind she's still in a relationship, albeit a not so good one; in the meantime, don't stop yourself from meeting/dating others...

---------- FOLLOW-UP ----------

QUESTION: Today we went out to lunch and I casually asked her if she and her boyfriend had reconciled. She said she's done with him. They broke up.
She did explain that in practice she and her now ex were already distant from one another. She would like to get married and have children before she turns 30. My friend also mentioned that she now feels awkward because she feels other people with less attributes of any sort are married or have a significant other. She said it would be nice if from out of nowhere someone asked her out (like at the gym, for instance).
That's when I decided to make my move and asked her out. She did agree to go out on Sunday but not "like a serious" date. I quickly asked "define serious" but I retreated from that position and let her speak some more. She said that she wants to go out "like friends".
She was accommodating since she went out of her way to explain that she had already made plans for Friday and Saturday but Sunday she's available.
I do like her as a friend; but I also believe she is a keeper. Any suggestions? Thanks

so she's essentially told you she sees you as a friend, no more, no less; see her as that if you choose, but keep expectations very low, as her feelings may never change, and you don't want to continually invest in this in the hope that this will someday be romantic...

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Over 20 years personal experience in dating, including both short and long-term relationships.Thoughtful reflection and analysis upon same, as well as providing imput relating to issues of love and romance to friends and acquaintances.

BA, Psychology, Bates College, Lewiston, Me. Graduate study at Fordham University School of Social Work.

Life experience can really be the only teacher in this area; however going through the experience is not enough. What is necessary is a real awareness, sensitivity to, and reflection upon what has happened, what has been lost, what has been gained. Getting beyond one's own insecurities and subjectivities, and seeing the experience in the context of the bigger picture, are essential stepping stones to learning and announces CT matchmaking service..for more, go to

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