Shy, inexperienced woman needs help getting things started with shy guy
September 13, 2015 7:22 PM Subscribe
I'm a woman in my mid-30s with very little dating or relationship experience. Several months ago I met a younger guy (early-mid 20s) and we've become gradually closer. We now exchange texts most days and have recently spent time alone together on a couple of occasions in frustratingly ambiguous contexts. (Is this a date? Search me.) I'm reasonably sure he's interested in me, and I'm positively sure I'm interested in him. But I need help moving things beyond this weird limbo stage.
I know he's had at least one long-term girlfriend in the past, but I get the impression that when it comes to women, he's nervous and risk-averse. I do think he's interested - several times I've caught him staring at me and then looking away quickly when I notice; he's shy and awkward around me in a way that he isn't with other people; he sends lots of unnecessary texts; and he's responded positively whenever I've suggested "hanging out" or have otherwise engaged with him. I have also confirmed that he's single.
The problem is that I am also quite risk-averse when it comes to dating. I've tried to be really clear with him that I'm interested, and I think he understands, but I don't think either of us know how to move things along.
When we spend time together, we have a great time and conversation is super easy. But toward the end of our time together, when it's time to go our separate ways, I think we both panic and flee. We've never had one of those awkward, end-of-date, are-we-going-to-kiss-now moments. We went to a movie one night (we drove separately) and we had about twenty minutes before the movie started when we sat in the nearly empty theater and talked and laughed with lots of prolonged eye contact. But the second we got outside after the movie was over, it was basically, "Okay, bye!" and we both fled to our cars.
I've accepted that I'm probably going to have to be the one to encourage this along. How do I do that? Or am I trying to rush things when I should just keep spending time with him and see what happens? Shy guys: How would you want a woman to handle this if you were in his position?
I know he's had at least one long-term girlfriend in the past, but I get the impression that when it comes to women, he's nervous and risk-averse. I do think he's interested - several times I've caught him staring at me and then looking away quickly when I notice; he's shy and awkward around me in a way that he isn't with other people; he sends lots of unnecessary texts; and he's responded positively whenever I've suggested "hanging out" or have otherwise engaged with him. I have also confirmed that he's single.
The problem is that I am also quite risk-averse when it comes to dating. I've tried to be really clear with him that I'm interested, and I think he understands, but I don't think either of us know how to move things along.
When we spend time together, we have a great time and conversation is super easy. But toward the end of our time together, when it's time to go our separate ways, I think we both panic and flee. We've never had one of those awkward, end-of-date, are-we-going-to-kiss-now moments. We went to a movie one night (we drove separately) and we had about twenty minutes before the movie started when we sat in the nearly empty theater and talked and laughed with lots of prolonged eye contact. But the second we got outside after the movie was over, it was basically, "Okay, bye!" and we both fled to our cars.
I've accepted that I'm probably going to have to be the one to encourage this along. How do I do that? Or am I trying to rush things when I should just keep spending time with him and see what happens? Shy guys: How would you want a woman to handle this if you were in his position?
Best answer: Use your face to make words. "Would you like to go on a date, a date-date, with me, specifically me?"
The answer to this question already exists. He either wants to do that or he does not, and neither of those answers will kill you. Finding out this answer is a great and wonderful thing, not a bad and terrible thing.
The best way to get around a lot of shyness is to speak plainly, honestly, and kindly. It really is. Nobody wins in a guessing duel to the death.
posted by Lyn Never at 7:37 PM on September 13, 2015 [20 favorites]
The answer to this question already exists. He either wants to do that or he does not, and neither of those answers will kill you. Finding out this answer is a great and wonderful thing, not a bad and terrible thing.
The best way to get around a lot of shyness is to speak plainly, honestly, and kindly. It really is. Nobody wins in a guessing duel to the death.
posted by Lyn Never at 7:37 PM on September 13, 2015 [20 favorites]
Ask him out. On a date.
If he invites you to do something, ask if it's a date.
I know this advice is thrown around a lot here at AskMe, but I recently used it to great effect.
FWIW the dude in question, in my case, apparently tried for over a year to ask me out by sending cryptic signs and asking me to hang out in nebulous date/friendly hangout grey areas. On what was going to be his very last try to get through to me, he asked me out for "dinner and a movie", which seemed much more date-like than most of our previous outings. So I finally got the ovaries to ask "is this a date?". He said yes, we went on that date, and now he's my boyfriend.
Re when to kiss, I typically remedy this by mentioning that I want to kiss the other person. It helps if you both know you're on a date. When I finally went out with the dude I mentioned above, we had just eaten dinner together and I said something like, "I've been overthinking our first kiss for a long time now, so I think we should just do it, right here, and not worry about it anymore." I'm not sure this would have worked on one of those grey area date/hangouts, though.
posted by Sara C. at 7:38 PM on September 13, 2015 [2 favorites]
If he invites you to do something, ask if it's a date.
I know this advice is thrown around a lot here at AskMe, but I recently used it to great effect.
FWIW the dude in question, in my case, apparently tried for over a year to ask me out by sending cryptic signs and asking me to hang out in nebulous date/friendly hangout grey areas. On what was going to be his very last try to get through to me, he asked me out for "dinner and a movie", which seemed much more date-like than most of our previous outings. So I finally got the ovaries to ask "is this a date?". He said yes, we went on that date, and now he's my boyfriend.
Re when to kiss, I typically remedy this by mentioning that I want to kiss the other person. It helps if you both know you're on a date. When I finally went out with the dude I mentioned above, we had just eaten dinner together and I said something like, "I've been overthinking our first kiss for a long time now, so I think we should just do it, right here, and not worry about it anymore." I'm not sure this would have worked on one of those grey area date/hangouts, though.
posted by Sara C. at 7:38 PM on September 13, 2015 [2 favorites]
Also I would not ask him out for coffee. You already know each other and are friends. He's not a potential serial killer. Just plain friends get coffee together all the time. Ask him out to do something that sounds like an obvious date.
posted by Sara C. at 7:41 PM on September 13, 2015 [1 favorite]
posted by Sara C. at 7:41 PM on September 13, 2015 [1 favorite]
omg he is going to be so happy when you just kiss him
posted by 256 at 7:43 PM on September 13, 2015 [14 favorites]
posted by 256 at 7:43 PM on September 13, 2015 [14 favorites]
Somebody needs to put a hand on somebody well before the end of the date. It's an unmissable signal of intention that doesn't require stressing about words. Sit next to each other (in a booth, say), gently lean into him a little, and see how he responds. If he doesn't twitch or jump, test things further by (again gently, but deliberately) touching his thigh or shoulder. You don't have to maul him, I'm talking millimeters. (Obviously stop if he twitches or jumps or leans away or says "please don't touch me".) Also, borrow a bit of liquid courage, unless there's a good reason to avoid that. (no more than 3 glasses)
*assuming you're on a date, definitely ask him out on something that is clearly a date
posted by cotton dress sock at 8:11 PM on September 13, 2015 [8 favorites]
*assuming you're on a date, definitely ask him out on something that is clearly a date
posted by cotton dress sock at 8:11 PM on September 13, 2015 [8 favorites]
omg he is going to be so happy when you just kiss him
Ugh, no. There's almost 0% chance this advice would be given if the genders were reversed.
There's been no mention of physical contact at all, according to the OP and the suggestion is just kiss him? There needs to be some kind of touching, a hug, holding hands, etc. to be sure of the context before going in for a kiss.
It's not even clear that they're on a romantic date.
posted by paulcole at 9:24 PM on September 13, 2015 [4 favorites]
Ugh, no. There's almost 0% chance this advice would be given if the genders were reversed.
There's been no mention of physical contact at all, according to the OP and the suggestion is just kiss him? There needs to be some kind of touching, a hug, holding hands, etc. to be sure of the context before going in for a kiss.
It's not even clear that they're on a romantic date.
posted by paulcole at 9:24 PM on September 13, 2015 [4 favorites]
Well, you could touch him when you're not on an official date, too, tbh. I'm not going to say it doesn't work just as well, if there's interest. But yes, I think light physical contact does help establish a context so that there isn't this huge cliffhanging moment at the end of the night. Try that kind of in the middle of the time you're together, once you've both loosened up a bit and are happy to be jabbering away. If it's returned, there will be a sort of natural progression. He might take a lead on the kissing part (a bit later).
Invite him to see a band (or some other similarly nocturnal, casual thing) on the weekend.
posted by cotton dress sock at 9:54 PM on September 13, 2015
Invite him to see a band (or some other similarly nocturnal, casual thing) on the weekend.
posted by cotton dress sock at 9:54 PM on September 13, 2015
You could invite him and make it an obviously romantic night without calling it a date beforehand. My suggestion: invite him over to your house and cook a nice dinner.
Set a table for two, light some candles, pour some wine, maybe make something in the oven so you can slip into a nice dress and later on serve one dessert with two spoons. I would hope that this would all be obvious enough for him to take the next step. Good luck!
posted by Fallbala at 1:28 AM on September 14, 2015
Set a table for two, light some candles, pour some wine, maybe make something in the oven so you can slip into a nice dress and later on serve one dessert with two spoons. I would hope that this would all be obvious enough for him to take the next step. Good luck!
posted by Fallbala at 1:28 AM on September 14, 2015
Certified shy guy writing here. I can relate to his risk-averseness. It can be rather demoralising for a man with little romantic experience when he has mustered the courage to make a bolder move with someone he believes is into him, just to find that he had mistaken her friendliness for attraction.
If I was interested in an older woman, had hanged around with her in ambiguous date/friends circumstances, and I was insecure about whether she wanted to escalate to a more romantic sort of thing, I would take her inviting me to dinner as a pretty clear message. If the proposed encounter was at your place, I think the message would be even clearer.
posted by samufer at 4:32 AM on September 14, 2015 [2 favorites]
If I was interested in an older woman, had hanged around with her in ambiguous date/friends circumstances, and I was insecure about whether she wanted to escalate to a more romantic sort of thing, I would take her inviting me to dinner as a pretty clear message. If the proposed encounter was at your place, I think the message would be even clearer.
posted by samufer at 4:32 AM on September 14, 2015 [2 favorites]
N-thing cotton dress sock's comment.
I had a similar awkward dating experience once - we'd hung out a few times but it was unclear whether we were actually dating, and it seemed like we were both too shy to make any kind of move since we weren't sure whether we were on the same page. Then one night when we were out having drinks together he kept touching my hand. It took a few touches until I finally realised "Oh, he's making a move". So I touched his hand back and then next thing I knew we were actually holding hands and by the time we left there was that palpable pre-kiss tension.
posted by kinddieserzeit at 4:52 AM on September 14, 2015 [1 favorite]
I had a similar awkward dating experience once - we'd hung out a few times but it was unclear whether we were actually dating, and it seemed like we were both too shy to make any kind of move since we weren't sure whether we were on the same page. Then one night when we were out having drinks together he kept touching my hand. It took a few touches until I finally realised "Oh, he's making a move". So I touched his hand back and then next thing I knew we were actually holding hands and by the time we left there was that palpable pre-kiss tension.
posted by kinddieserzeit at 4:52 AM on September 14, 2015 [1 favorite]
There's almost 0% chance this advice would be given if the genders were reversed.
But they're not.
Kiss at will.
posted by flabdablet at 5:43 AM on September 14, 2015 [1 favorite]
But they're not.
Kiss at will.
posted by flabdablet at 5:43 AM on September 14, 2015 [1 favorite]
There's almost 0% chance this advice would be given if the genders were reversed.
But they're not.
Kiss at will.
I would like to add that, in this circumstance, a hand on the knee/thigh is a good precursor to the kiss. If he recoils from the hand then you can change plans and recover gracefully. But he won't.
After the kiss is successful, ask him to stay the night. Life is too short to take things slow.
posted by 256 at 6:23 AM on September 14, 2015
You could invite him and make it an obviously romantic night without calling it a date beforehand. My suggestion: invite him over to your house and cook a nice dinner.
I think this is good idea and what my now-partner did. We had been going out for dinners, drinks and plays for a few months but they were not "dates" as far I thought. I though she just wanted to be friends and she thought I just wanted to be friends. We both were actually interested in more.
So one night, she invited me to her place for dinner. That was the signal I needed and a kiss happened during the appetizer stage. We are very happy now and joke about how long it took to get together.
(We are the same gender, but I don't think this matters.)
posted by Lescha at 10:36 AM on September 14, 2015 [1 favorite]
I think this is good idea and what my now-partner did. We had been going out for dinners, drinks and plays for a few months but they were not "dates" as far I thought. I though she just wanted to be friends and she thought I just wanted to be friends. We both were actually interested in more.
So one night, she invited me to her place for dinner. That was the signal I needed and a kiss happened during the appetizer stage. We are very happy now and joke about how long it took to get together.
(We are the same gender, but I don't think this matters.)
posted by Lescha at 10:36 AM on September 14, 2015 [1 favorite]
Does anyone dance anymore? The dance floor is a great place to break the ice.
posted by SemiSalt at 4:04 PM on September 14, 2015
posted by SemiSalt at 4:04 PM on September 14, 2015
Do ask him to go on a date.
Don't just kiss him. If he is very shy, that might cause him extreme embarrassment and have a counter-productive effect.
Ask him on a date, then judge whether kissing might be an appropriate next step.
posted by robcorr at 10:09 PM on September 14, 2015 [1 favorite]
Don't just kiss him. If he is very shy, that might cause him extreme embarrassment and have a counter-productive effect.
Ask him on a date, then judge whether kissing might be an appropriate next step.
posted by robcorr at 10:09 PM on September 14, 2015 [1 favorite]
When I was unclear as to whether my now-girlfriend was interested in me romantically after our first date, I asked her via text. She called and made it clear that she was into me and wanted to see me again. We exchanged a lot of messages in between the first and second date that further clarified our mutually amorous intentions. On the second date, she claims that I asked, "Can I kiss you?" I don't remember it that way, but whatever I said apparently worked just fine. We kissed.
After two more weeks of heavy dating, I asked her if she wanted to be my girl. She said yes.
posted by Gray Skies at 9:48 AM on September 15, 2015
After two more weeks of heavy dating, I asked her if she wanted to be my girl. She said yes.
posted by Gray Skies at 9:48 AM on September 15, 2015
Response by poster: Thank you all! I asked him out using the word "date." Alas, he said he thinks we're better as friends. I'm disappointed, but so glad I have an answer and can put an end to the confusion and awkwardness.
posted by SoLongLivesThis at 3:06 PM on September 17, 2015 [3 favorites]
posted by SoLongLivesThis at 3:06 PM on September 17, 2015 [3 favorites]
This thread is closed to new comments.
posted by lefty lucky cat at 7:27 PM on September 13, 2015 [1 favorite]