To Try to Date, or not try to Date?

iVillage Member
Registered: 05-02-2014
To Try to Date, or not try to Date?
12
Fri, 05-02-2014 - 5:08pm

I've had a disasterous dating life. Im now 40 years old, and have never been in a serious relationship. I was pretty shy, anxious and awkward around men for a long time. I have worked on low self esteem and anxiety for several years through therapy and with anti depressants. Even though I am a party loving extrovert, I have rarely been asked out on dates. A few one night stands but never when I was sober, and usually a friend or brother of a friend who turned out to alread be in a relationship.

I hav tried online dating for a few years, never met anyone that for me: some were okay, but some impolite, full of themselves or just didnt seem to like the idea of being there. Several said they thought I was nice but too old, as at 35 i was too old to have children. I basically stopped OLD : I dont think men like OLD unless its for sex. Maybe it makes them feel less virile or powerless?

SO...after years of this nonsense, after I turned 36, I resigned myself to the fact I'd not have a family/children and probably needed to get used to being alone.

Of course, as I have got older I have no problem being shy or awkward and its MUCH less stressful.I wish I wasnt single but I am.  But I have a busy work life and meet a lot of people. And a few guys I have met through work in the different cities I work in have been in touch, suggesting dinner or a drink if I am back in that city. On one occasion I declined after a work meeting, as I had a huge deadline. Another guy in another city has been in touch for months but our diaries never coincide...and I admit I kind of put him off as he seemed quite serious.

I am luke warm about the two of them. But then 2 mths ago I met a great guy I really liked : we talked for several days on an assignment, went for a drink or two and tallked for hours and hours, had lots in common. I thought he seemed kind of into me. It felt very normal. and I really really found him interesting, fun, and bright. We both left the country - saying we would stay in touch. But he didnt even reply to an email I sent (yes, I waited 3 days and then I did send him an email first!!!!) or seem to want to get in touch. I actually went through the whole "does he like me? will he ever call?" checking my emails 10 times a day. Nothing. He was in a serious relationship until 18 mths ago, and I know he is single again. Guess he didnt even want to stay friends?

I ask myself: why do I do this? Isnt it easier to not like anyone??!!!!  So Ive not even followed up with the other two guys - Im not even sure i liked them. 

Yesterday at a party a really cute guy (married, late 40s) who is here on business.  Ive met him a few times through friends  before. This time he asked me why i was single. I said I was probably quite shy when I was younger. He said he thought I was funny and confident and liked chatting to me - he didnt see any problem at all, I seemed fine. I was kind of embarrassed. He wasnt any more fliratious than I was with him (arms around each others shoulders a few affectionate squeezes) but then he invited me back to his hotel ...I went in a casual kind of way and it was fine. We chatted for ages. But I made sure I was appropriate, not overtly sexual or flirattious and even after a few drinks I was very very conscious of not assuming he wante sex, Noting happened (we talked) I left at about 3am to go home. I didnt get any vibe that he was trying to have sex. In some ways I think I was a bit dismissive of certain things (dumb women, girls who cry, people who are over emotional). I think part of him may have been shocked, and maybe he even disliked me for it. I have seen him since and he seemed a bit distant.

I feel a bit silly now. Was that silly to even worry about what i was doing? I know I was maybe harsher than I nornally am,and I feel DUMB.  But it doesnt matter, if hes married, right as I wasnt even interested (or maybe I kind of was but didnt even let that thought develop). I stopped myself thinking "what could have happened? should I have tried to push it a bit?" after all, Im not getting sex with anyone else!!

And what about these other two guys? Next time should I just meet them for fun, or try to have a one night stand, or just go along with anything  cos theres nothing better? I know Im slightly overweight at the moment and so I feel less confident than usual.

But Im not sure whether to even think aboiut dating again or not? I feel every day now Im getting older, missing any chances. if I get some attention now, it will surely only get worse as I get older? I hate the pain of attraction, dating etc. Maybe thats w hy i was dismissive to the hotel guy? In reality I know Id like to not be single, and meet these guys, but I still feel the SHY me inside, feeling awkward, lpow self esttem (which i still struggle with)

People say " when it feels right its easy". Ive said that all my life - and so far NOTHING that has felt vaguely right has worked out with any guy and it seems like an awful lot of pain for something that other people seems so easy - even people who dont seem to have much going for them or have no confidence or seem REALLY needly and unstable.

I *really* dont know what to do. Do I need a tactical change. Tor date or not to date? that is the question. Remember I'm bad at it and it only leads to awkardness and pain.

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iVillage Member
Registered: 11-28-1999
Fri, 05-02-2014 - 8:50pm

If you go into dating thinking that things will inevitably turn out badly, they probably will.  Yes, a lot of times it happens but you can't start out thinking in a negative way.  And 40 is definitely not too old to find someone.  I have many friends who got divorced and then met their current BFs after they turned 40.  By that time, men your age will probably not be thinking about having kids so it won't matter that  you are probably too old to have kids.

Now I certainly think that you shouldn't have pursued the married man, even for a ONS.  Why would you even go there?  As far as the guy you met 2 months ago who you really liked, you said that you both "left the country," so I assume that you would be very long distance--it was really rude of him to stop talking to you but maybe he thought about it and just realized that being long distance, things wouldn't work out.

I think for someone who hasn't had much of a dating life OLD can be pretty harsh because most of the guys you will meet won't work out, some are married, some are con artists, etc.  I think the best way to meet someone would be to find an activity that you like where you could actually get to know men in a situation where you don't have to date--a professional group, a meetup group, sports, etc.  You could get to know men as friends first and then see what develops.  Good luck.

Avatar for sabrtooth
iVillage Member
Registered: 12-03-1999
Sat, 05-03-2014 - 12:49pm

Youy say you were "...shy, anxious and awkward around men for a long time. I have worked on low self esteem and anxiety for several years through therapy and with anti depressants...", which has morphed you into a "...party loving extrovert...", given to drunken one night stands, "...usually (with) a friend or brother of a friend who turned out to alread be in a relationship...".  Then you meet a man while you BOTH are in another country.  You went drinking, and talked for "...hours and hours...".  Where?  In his hotel room?  Then you meet a MARRIED man, who thought you were "...funny and confident and liked chatting to me...".  In fact, you were such an amazing conversationalist, that this married man invited you back to his HOTEL ROOM, to CHAT till 3AM. 

You choose inappropriate men, in inappropriate locations, go drinking with them, send them wildly mixed signals, and then expect it to turn into a relationship.  You need to get some good counseling, and find out what is REALLY going on in your head.  Fix yourself, and the rest will follow.

iVillage Member
Registered: 05-02-2014
Sat, 05-03-2014 - 3:57pm

Sabrtooth: I am not sure what you mean by "wildly mixed signals"? I feel a bit insulted as I wasnt under the impression i was being crazy or needed "fixing".

Maybe I wasnt clear: I like to talk. I  have always enjoyed platonic male company  (I often find women too petty, b**chy, and manipulative)., and have many male friends. I know that generaly I feel comfortbale with men who I think are UNAVAILABLE.....ie they arent interested in me, or else I know they arent attracted to me, or are married or whatever - ie if its not on the cards. Hence my disasterous/non existence dating record.

I feel awkward if I think someone likes me  as I dont know what to do - should I try to "make" him like me? And when I think they do like me and it goes wrong,  I find it painful to deal with rejection (I have had a lot) and beat myself up over what I ma have done (even if it was nothing.  BUT... I have seen girls go CRAZY and almost have breakdowns after being stood up or refjected even afetr one night stands. Believe me, I have met some totally unstable women with toxic relationships with men. I can definitely say that is NOT me!

 Im not uptight, I dont play games, and my friends (male and female, of all ages) tell me I am  uncomplicated, straightforward, positive and laid back. I hate it when things are made into a big deal, I prefer a more gentle approach to life. I know I am pretty, funny and well educated (even though I dont boast or "know it').

 I am  not someone who just flirts/hooks up ( Ive only done that 4 or 5 times in total not a regular weekly habit! I dont think id ever have been successful enough even if I had wanted to!!!!! )

But Sabretooth: surely you would understand that its nice to have some male attention and flattery? Even if neither of intended anything to happen (and it didnt) No, I didnt talk to this guy I liked so much in his hotel room! We were there for work and have a mutual friend (who actually was the one who pushed us to definitely meet and talk as she thought we would hit it off). We were with other colleagues and only at one point alone maybe for 30 mins, in a bar. Nothing happened.

I wanted to kind of indicate I liked him, but how does one do that??? Its too difficult!

Music lover - thanks for your wishes. I like joining clubs and normal activities:  I go to salsa classes and a book club, as well as gym classes and previously a mucis group and language evening classes. I have taken cooking classes too.  I just find that after doing these sorts of things my whole life, Im starting to feel I really ought to get a hint from some external power ......and resign myself to the fact that despite lots of male and female friends, a lovely social life,  I will be on my own forever. Should I give up? That was the reason for my posting.....

Avatar for sabrtooth
iVillage Member
Registered: 12-03-1999
Sat, 05-03-2014 - 6:01pm

"... I am  not someone who just flirts/hooks up ( Ive only done that 4 or 5 times in total... )...".  This is a contradiction-- mixed signals, if you will.   The average woman does NOT hook up with one night stands.  Once is a mistake.  4 or 5 times, when drunk, and with inappropriate men, is a problem.  And the fact that you are in denial is also a problem. 

Most women realize that male business associates, whom you meet out of town, or who meet you when they are out of town,  who "chat" for hours, and take you for dinner and drinks, are NOT looking for "friends".  They are looking to hook up.  So after you eat, drink, and chat, and then say NO SEX, you are sending mixed signals. And of course these men will not call you once they leave town.

The average single woman, looking for a real relationship, will not waste her time chatting up a married man.  The average woman also understands that married men who shower you with compliments, chat you up, and invite you back to their hotel rooms are NOT looking for conversation.  When you go to their hotel room, then say NO SEX, you are sending mixed signals.  And why are you upset that a MARRIED MAN was distant toward you the following day?  You say you want a real relationship, then act like you want an affair, and are upset that it didn't happen.  More mixed signals.

Yes, it's nice to have male attention and flattery.  But when you say you "...generaly(sp)... feel comfortbale(sp) with men who I think are UNAVAILABLE.....ie they arent interested in me, or else I know they arent attracted to me, or are married or whatever..", then you are  "...looking for love in all the wrong places...", and with the wrong kinds of men.  And when you do that, don't you understand that men will make certain assumptions about you?  And that the "right" kinds of men will be put off?  What exactly do you think a single man at that party, who might have been interested in you, is thinking about you when he sees you falling all over a married man, and then leaving with him?

YOU SAY that you "...feel awkward if I think someone likes me  as I dont know what to do - should I try to "make" him like me?...".  If you are over the age of 16 and still feel awkward if you think someone likes you, if you don't know how to start a real relationship, and if you think you can "make" someone like you, then you have a problem.  Being in denial that you have a problem, is a problem.  If you want those problems fixed, you need counseling. 

iVillage Member
Registered: 02-25-2013
Sun, 05-04-2014 - 9:51am

Living life in a supposed bubble of safety to avoid hearbreak brings you the results of being a lonely person. In one book I read on the secrets of happiness, a survey was given to numerous elderly people who were asked about regrets during their lifetimes. They regretted things they didn't attempt, and were happy they took the risks they did, even if it didn't pan out.

Sounds like you're sabotaging yourself by your behavior when you meet someone who might be a good candidate for dating. Do not project forward to the future while on a date. Have the goal of enjoying yourself by merely getting to know the other person. Keep the subjects light, and take interest in him by asking, "Do you like to play or watch sports? What do you like about your job?" Avoid controversial subjects or intrusive or serious questions. Keep the subject matter light on yourself as well. Tell him a few job duties you perform at work. Tell him what hobbies you like or that you like to cook, etc. Be yourself, and know that when you are authentic, eventually you will meet the right man who appreciates you just as you are.

Ask friends if they can help you out by telling you if they see something off-putting about how you behave around men. Tell them you want to be successful in dating and want to know if it's something you're doing that you're not aware of. Never chase a man or make the first move. A man who is interested just needs a green light from you as simple as a smile or touching his arm and telling him you like his shirt.

Just know that it's more rare than common to meet someone and you both have chemistry, share the same values/ethics, life goals, and meet each others major needs. If it doesn't work out, then one or more of those things are lacking, and it has to end. Don't think of it as rejection. Most people have to date a boatload of people before they find "the one." Yes, it's frustrating and hurtful when people go their separate ways, but that's life. Nobody said it was easy. After my divorce, I dated about 30 men over a period of several men, most from OLD, and most didn't go beyond the first date. As horrible as things were, I kept plugging away until I found a man who would eventually become my husband. We were so comfortable together and everything fit like the pieces of a puzzle and we're very happy. If I had given up by date 5, 12, or 29, I'd be alone right now. Read some books on relationships and try some new meetups on meetups.com.  Good luck.

iVillage Member
Registered: 11-28-1999
Sun, 05-04-2014 - 10:40am

Sabr,

She already said that she didn't go to the married guy's hotel room, yet you repeated again as if she did.  Yes, I agree that there are many business travelers who are looking for hookups while away from home.  But there are also single people who also might be looking to date someone.  I don't think there is anything wrong with dining and chatting with a business colleague and not having sex and I don't think that is sending mixed signals at all, if all you are doing is going out to dinner.  I would think it would be very presumptuous for a man to assume that just because a woman accepted his invitation to dinner and drinks that she must be saying that she is going to have sex with him.  Now going back to a guy's hotel room is a different story.  

There was a guy I used to chat with on IV--we eventually exchanged phone nos. and personal info.  He came to my city on business and we had a nice dinner at his hotel--he paid (cause he is rich).  Neither of us is romantically interested in the other.  I am 10 yrs older than him.  It was just nice to get together and talk.

iVillage Member
Registered: 11-28-1999
Sun, 05-04-2014 - 10:45am

It's hard to say whether one should give up or not.  I'm older than you and feel that with age, it just gets harder and harder to date since a lot of men are looking for younger women and I certainly don't want some old man with health problems who doesn't want to go out after 9:00 pm.  I am not making an effort to really meet someone, for ex, I don't really like online because I didn't like the way it made me feel--too much rejection!  So I just go out and do what I like.  I still hope that someday I will meet someone but I try to arrange my life so that if I don't meet someone I am still having fun.

Avatar for sabrtooth
iVillage Member
Registered: 12-03-1999
Sun, 05-04-2014 - 1:12pm

nyc2001 wrote:
<p><p>Yesterday at a party a really cute guy (married, late 40s) who is here on business.  Ive met him a few times through friends  before. This time he asked me why i was single. I said I was probably quite shy when I was younger. He said he thought I was funny and confident and liked chatting to me - he didnt see any problem at all, I seemed fine. I was kind of embarrassed. He wasnt any more fliratious than I was with him (arms around each others shoulders a few affectionate squeezes) but then he invited me back to his hotel ...I went in a casual kind of way and it was fine. We chatted for ages. But I made sure I was appropriate, not overtly sexual or flirattious and even after a few drinks I was very very conscious of not assuming he wante sex, Noting happened (we talked) I left at about 3am to go home. I didnt get any vibe that he was trying to have sex.   But it doesnt matter, if hes married, right as I wasnt even interested (or maybe I kind of was but didnt even let that thought develop). I stopped myself thinking "what could have happened? should I have tried to push it a bit?" after all, Im not getting sex with anyone else!!</p>.</p>

Well, in her first post she said she DID flirt with the married man, and DID go back to the married man's hotel room.  And had a few drinks there.  And stayed there till 3am.  And said she wondered if she should have had sex.  And said she did this YESTERDAY.  And then said she was NOT someone into flirty/hookups.

Music, my husband traveled with several jobs, often out of the country, for years.  I traveled with my first career.  We both have friends and associates who also travel.  Business travelers who are NOT looking for hookups, are very circumspect.  They are well aware of their reputations, and how things may be interperted--especially by their company, should word get back.  They do NOT go traveling with the hope they will meet someone to date, most particularly because God Knows when they will be able to see an out-of-towner again. 

Your situation was different.  In the first place, you had a relationship with the man BEFORE he came to your city.  You didn't sit next to a stranger in a conference or business meeting, chat with him for a while, agree to go for drinks with him--and then expect it to turn into a relationship.

Avatar for xxxs
Community Leader
Registered: 01-25-2010
Sun, 05-04-2014 - 8:35pm

 Are you a motor mouth?  You mentioned "like to talk" and that thought jumped into my mind.  And do you know "manspeak"?    I suggest a therapist to help you figure this out.  It seems some behaviour is working to cross purposes.

chaika

Avatar for khatru1
iVillage Member
Registered: 06-07-2004
Wed, 05-07-2014 - 10:52am

I guess you have to ask yourself what you want. If you want to be single then stop dating and/or trying to date. If you do not want to be single then do not stop trying. It kinda sounds to me like you do not want to be single so keep trying, pressing forward. You have to fight through the jerks, the ones only looking for a good time, etc. Brush off the ones who do not work out, don't worry about the ones who disappear on you. Stay the course. If it was so easy to find someone then there wouldn't be the proliferation of dating sites out there that there currently is. What's the old saying, nothing so easily gained is likely worth having.

There are many women in your shoes. Also keep in mind there are many who have someone but in reality are not happy in their relationship. Looks can be deceiving in this regard. You do not want a guy so you can hang a sign on yourself saying I have someone, you want a guy so you can have an awesome relationship.

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